Overview of reaction types organic reaction database
| Reaction name | Description | namespace | Count | |
|---|---|---|---|---|
| 1,2,3 triazole synthesis | Any reaction forming an 1,2,3-triazole ring system from a carbonyl containing compound and an amine. | i | 29 | Go |
| 1,2,4 triazole synthesis | Any reaction forming an triazole ring system. | i | 1234 | Go |
| 1,2,4-oxadiazole synthesis | Any reaction forming a formal 1,2,4-oxadiazole ring. | i | 2772 | Go |
| 1,2-dihaloalkene reduction | Conversion of a 1,2-dihaloalkene to a monosubstituted haloalkene. | i | 174 | Go |
| 1,3,4-oxadiazole synthesis | Any reaction forming a formal 1,3,4-oxadiazole ring. | i | 1837 | Go |
| 1,3-dipolar cycloaddition | A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound. | i | 1 | Go |
| 2H-chromene synthesis from terminal alkyne | Aromatic substitution reaction and intramolecular ring-closing reaction of a phenyl propargyl ether to form a 2H-chromene. | i | 44 | Go |
| acetal forming reaction | The acid-catalyzed formation of an acetal (or ketal) by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water. Common purpose: protection of either carbonyl group or diol | i | 2 | Go |
| Acetylation | Adding a (protective) acetyl group to a hydroxyl group. Source: Wikipedia | i | 1969 | Go |
| Achmatowicz rearrangement | A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised. | i | 3 | Go |
| Acid alkylation with diazo compounds | With diazo compounds acids react to esters, with diazomethane the reaction product is a methyl ester. (March 0-28) | i | 616 | Go |
| Activation reaction | Any reaction that activates amines and alcohols for subsequent substitution reactions for example as a mesylate or triflate | i | 13808 | Go |
| acylation | Formation of a covalent bond between a substrate and an acyl group. | i | 112 | Go |
| Addition reaction at alkenes | Addition reaction (electrophilic or nucleophilic) at a carbon carbon double bond. Formation of an ether (but not epoxides) with alcohols. Formation of an ester from a carboxylic acid. See also: alcohol protection with pyrans. | i | 191 | Go |
| addition reaction step | A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. | i | 34 | Go |
| Addition–elimination reaction | Any reaction involving a nucleophilic addition followed by an elimination reaction (Wikipedia) | i | 1063 | Go |
| AES dehalogenation | Replacement of an aromatic halogen by hydrogen. Reagents: Friedel-Crafts catalysts, catalytic hydrogenation. Source: March 1-45 | i | 1145 | Go |
| alcohol oxidation to carboxylic acid | An alcohol oxidation where the alcohol centre is replaced with a carboxy group. | i | 618 | Go |
| Alcohol protection with pyrans | Addition reaction of an alcohol to a pyran leaving a protected alcohol. | i | 840 | Go |
| aldehyde reduction | A reduction in which an aldehyde is reduced to form a primary alcohol. | i | 3865 | Go |
| Aldehyde to carboxylic acid oxidation. | Any conversion of an aldehyde to a carboxylic acid. | i | 984 | Go |
| aldol addition | A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol. | i | 78 | Go |
| aldol condensation | An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone. | i | 399 | Go |
| Aliphatic dehalogenation | Reduction of alkyl halides with dehydrohalogenation. Hydro-de-halogenation (March 0.77) | i | 196 | Go |
| Aliphatic nucleophilic substitution | Reaction of a nucleophile for example a bromine anion with an aliphatic substrate with a good leaving group | i | 21311 | Go |
| Aliphatic nucleophilic substitution at activated oxygen | Reaction of a nucleophile with an activated oxygen electrophile, for example a tosylate or mesylate forming ethers, amines and azides. | i | 2459 | Go |
| alkene cyanation | Converts alkenes to nitriles by action of a cyanide. With hydorgen cyanide the reaction is a hydrocyanation Source: Wikipedia. | i | 3 | Go |
| Alkene dehydrohalogenation | Conversion of an vinyl halide to an alkyne (March 7.14) | i | 108 | Go |
| alkene metathesis | A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. | i | 5 | Go |
| alkene oxidative cleavage | An alkene oxidation where the carbon-carbon double bond is cleaved. | i | 2 | Go |
| alkene ozonolysis | An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide. | i | 7 | Go |
| alkene reduction to alkane | A reduction where an alkene is reduced to an alkane using classical reducing agents. See also hydrogenation | i | 931 | Go |
| Alkoxycarbonylation | Organic reaction between an aryl or alkenyl halide, carbon monoxide and an hydroxide forming an ester. Also includes reactions with methyl cyanoformate (Mander's reagent) and a strong base. | i | 43 | Go |
| Alkylation at active-hydrogen alpha carbon | Alkylation reaction on substrates carrying a carbon atom with active hydrogen of the type Z-CH2-Z. Malonic ester synthesis excluded. Source: March 0-96 | i | 112 | Go |
| Alkylation of ketones, nitriles and esters | Alkylation by alkyl halides of ketones, esters and nitriles at alpha carbon position. Other functional groups may apply. requires strong base. With carbonyl groups the enolate conjugate base is involved, Source: March 0-97 | i | 4584 | Go |
| Alkyne 1,2-addition | 1,2-additions over an alkyne by amines and alcohols to form enamines and enols | i | 71 | Go |
| Alkyne deprotection | Alkyne deprotection with removal of trimethylsilyl group. | i | 2264 | Go |
| Alkyne hydration | Formation of aldehydes and ketones by hydration of alkynes. Can be catalysed by mercury salts. Source: March 5-3 (dihydro-oxo-biaddition) | i | 95 | Go |
| alkyne reduction to alkane | A hydrogenation reaction where an alkyne is reduced to an alkane. | i | 1332 | Go |
| Alkyne to alkene reduction | Any reaction reducing an alkyne to an alkene | i | 708 | Go |
| Alkyne trimerisation | a [2+2+2]cycloaddition reaction in which three alkyne units react to form a benzene ring, requires a catalyst. Source: Wikipedia | i | 3 | Go |
| alkyne-azide click reaction | A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed. | i | 152 | Go |
| Amide dehydration to a nitrile | Conversion of an amide to a nitrile, commonly with phosphorus pentoxide (March 7.42) | i | 2519 | Go |
| Amide hydrolysis | Amide hydrolysis other than BOC deprotection, amine group retained or carboxylic acid group retained | i | 10832 | Go |
| amide reduction to amine | A reduction process where an amide is transformed into an amine. | i | 2841 | Go |
| amination | Formation of a covalent bond between a substrate and an amino group. | i | 3199 | Go |
| amine oxidation to a nitro group | Any reaction converting an amine group to a nitro group. Why exactly? | i | 131 | Go |
| Amine oxidation to ketone | Amine oxidation to ketone. As per 3,5-di-tert-butylcyclohexa-3,5-diene-1,2-dione (Corey & Achiwa) | i | 2 | Go |
| Amine salt formation | Amines react with acids (HCl, carboxylic acids) to form ammonium salts. (Source: Wikipedia) | i | 6 | Go |
| amino group deprotection | A deprotection reaction where the reactive centre is an amino nitrogen atom e.g. tert-butylsulfinyl, BOC deprotection excluded. | i | 14525 | Go |
| amino group protection | A protection reaction where the reactive centre is an amino nitrogen atom. | i | 1590 | Go |
| Aminocarbonylation | Organic reaction between an aryl halide, carbon monoxide and an amine forming an amide. | i | 6 | Go |
| Anhydride synthesis | Any reaction forming an anhydride C(=O)OC(=O) intramolecular or intermolecular | i | 239 | Go |
| annulation reaction | annulation reactions [5+2], [3+2] | i | 2 | Go |
| Appel bromination | Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine. | i | 2159 | Go |
| Appel chlorination | Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane. | i | 196 | Go |
| Appel halogenation | Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source. | i | 1 | Go |
| Appel iodination | Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane. | i | 536 | Go |
| Aromatic amino-de-halogenation | Reaction of an aryl halide with an amine catalysed by copper or nickel. (March 3-6) | i | 1751 | Go |
| Aromatic halogen exchange reaction | Any reaction converting an aromatic bromide or chloride to an aromatic iodide | i | 493 | Go |
| Aromatic nitration | A reaction that adds a nitro group to an aromatic ring involving an nitronium ion | i | 3828 | Go |
| Aromatic sulfonation | Formation of an sulfonic acid from an arene and a sulfonation reagent for example sulfuric acid or sulfur trioxide. (Source: Wikipedia) | i | 131 | Go |
| Aromatization | Any reaction in which an aromatic system is formed from a single nonaromatic ringsystem. Source: Wikipedia | i | 7 | Go |
| Aryl-aryl Grignard coupling | A reaction of an aryl Grignard reagent with an aryl halide forming an aryl - aryl coupling adduct. Also Kumada coupling. | i | 69 | Go |
| arylation | Formation of a covalent bond between a substrate and an aryl group. Reagents: organobismuth compounds. | i | 8 | Go |
| atom transfer radical cyclization (ATRC) | Cyclization reaction between an alkene and an aliphatic halide catalysed by a copper catalyst | i | 1 | Go |
| aza-Diels-Alder reaction | A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound. | i | 8 | Go |
| aza-Wacker cyclisation | A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. | i | 1 | Go |
| Azacycle synthesis by imine formation | Any condensation between a an amine and a carbonyl group containing compound forming a new nitrogen containing 5,6 or 7 membered cycle for example a pyrimidine, see also pyrrole synthesis | i | 299 | Go |
| Azide formation | Any reaction forming an azide. Includes nucleophilic substitution by sodium azide. | i | 427 | Go |
| Azido-de-diazoniation | Conversion of an diazonium salt to an azide by the addition of sodium azide (March 3-23) | i | 1 | Go |
| Baeyer-Villiger oxidation | A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step. | i | 73 | Go |
| Bamford-Stevens reaction | The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin. | i | 15 | Go |
| Barton decarboxylation | The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione. | i | 5 | Go |
| Barton-McCombie deoxygenation | The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism. | i | 29 | Go |
| Baylis-Hillman reaction | A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound. | i | 2 | Go |
| Beckmann rearrangement | A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group. | i | 51 | Go |
| benzimidazole synthesis | A reaction in which the intended product is a benzimidazole that was not present in any of the reactants. | i | 1738 | Go |
| benzoin condensation | A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone). | i | 54 | Go |
| Benzyl alcohol reduction | Reduction of an aromatic methyl alcohol group to a methyl group | i | 14 | Go |
| benzyl ether deprotection | A hydroxyl group deprotection where benzyl group is removed from an benzul ether liberating the alcohol | i | 159 | Go |
| benzylamine deprotection | An amino group deprotection reaction where a benzyl group is removed. | i | 5313 | Go |
| benzylic oxidation | An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. | i | 1 | Go |
| beta-haloacrylonitrile synthesis | Any reaction forming a beta-haloacrylonitrile | i | 25 | Go |
| Birch reduction | Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia. | i | 5 | Go |
| Bischler-Napieralski reaction | A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline. | i | 111 | Go |
| Boc deprotection | An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions. | i | 59653 | Go |
| Boc protection | A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound. | i | 10748 | Go |
| Boronic ester hydrolysis | Any reaction converting a boronic ester to an boronic acid. | i | 380 | Go |
| bromo Heck-type reaction | A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin. | i | 641 | Go |
| bromo Sonogashira coupling | A Sonogashira coupling where the aryl halide is an aryl bromide. | i | 1645 | Go |
| bromo Suzuki coupling | A Suzuki coupling where the halide is a bromide. | i | 33296 | Go |
| Buchner ring expansion | a carbon-carbon bond forming reaction used to synthesise 7-membered rings from 6-membered rings with formation of a carbene from a ethyl diazoacetate. Source: Wikipedia | i | 3 | Go |
| Buchwald-Hartwig amination | A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst. | i | 18099 | Go |
| Burgess dehydration reaction | Type of elimination reaction converting an alcohol to an alkene using methyl N-(triethylammoniumsulfonyl)carbamate | i | 2 | Go |
| C-H activation | A type of organic reaction in which a carbon–hydrogen bond is cleaved and replaced with a C-C, C-O or C-N bond in the presence of a transition metal (Source: Wikipedia) | i | 2 | Go |
| Carbamate reduction | Reduction of carbamates ROC(=O)NRR to an amine HNRR with reducing agent (dihydrogen) and catalyst (Pd) | i | 3945 | Go |
| Carbene reaction | Any reaction involving a carbene as reactive intermediate | i | 10 | Go |
| carbon-carbon coupling reaction | A reaction where a bond is formed between two carbon atoms. | i | 8 | Go |
| carbonyl compound to imine conversion | A functional group modification where a carbonyl compound is converted to an imine. With an α-carbonyl proton present the reaction product is an enamine (Alkylimino-de-oxo-bisubstitution) | i | 10706 | Go |
| carbonyl group protection | A protection reaction where the reactive centre is a carbonyl oxygen | i | 497 | Go |
| carbonyl methylidenation | The conversion of an carbonyl group to an methylene group. Reagent: Tebbe's reagent. Alternative to Wittig reaction | i | 28 | Go |
| Carbonyl thiation | Conversion of carbonyl compound to thioketone, with for example Lawesson's reagent | i | 1530 | Go |
| Carboximidamide synthesis | Conversion of an imine or nitrile to a carboximidamide | i | 425 | Go |
| carboxy group deprotection | A deprotection reaction where the reactive centre is a carboxy oxygen atom. | i | 2569 | Go |
| Carboxylate salt formation | Carboxylic acids react with bases to form carboxylate salts, in which the hydrogen of the hydroxyl (–OH) group is replaced with a metal cation. (Source: Wikipedia) | i | 843 | Go |
| carboxylation | Formation of a covalent bond between a molecule and a carboxy group. | i | 204 | Go |
| carboxylic acid benzyl ester deprotection | carboxylic acid benzyl ester deprotection, for example with hydrogen / palladium | i | 2888 | Go |
| carboxylic acid to acid chloride conversion | A functional group modification where a carboxylic acid is converted to an acid chloride. | i | 5791 | Go |
| carboxylic acid to primary alcohol reduction | A carboxylic acid reduction where the product is the corresponding primary alcohol. | i | 4256 | Go |
| Carroll rearrangement | An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst. | i | 1 | Go |
| Castagnoli-Cushman reaction | Condensation reaction of cyclic anhydrides with imines forming an isoquinoline | i | 10 | Go |
| Catalysed nucleophilic aromatic substitution with S-nucleophiles | a palladium, copper catalysed substitution reaction in which an sulfur nucleophile displaces a good leaving group, such as a halide, on an electron deficient aromatic ring. | i | 74 | Go |
| Chan-Lam coupling | Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. | i | 510 | Go |
| Chiral resolution | Any chemical process bringing about the separation of a racemic mixture into enantiomers. Requires a chiral resolving (derivatizing) agent. Source: Wikipedia. | i | 25 | Go |
| chloro Heck reaction | A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium. | i | 37 | Go |
| chloro Sonogashira coupling | A Sonogashira coupling where the aryl halide is an aryl chloride. | i | 217 | Go |
| chloro Suzuki coupling | A Suzuki coupling where the halide is a chloride. | i | 10623 | Go |
| Chugaev reaction | Elimination of a water molecule from a secondary alcohol to yield an olefin. | i | 1 | Go |
| Claisen condensation | A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester. | i | 110 | Go |
| Claisen rearrangement | The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound. | i | 3 | Go |
| Cleavage of an N-trimethylsilylmethyl group | Cleavage of an N-trimethylsilylmethyl group to an N-methyl group can be rought about by TBAF. | i | 40 | Go |
| Clemmensen reduction | A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid. | i | 2 | Go |
| Colvin Rearrangement | homologization and addition of lithiated TMS diazomethane to aldehydes to form an alkyne | i | 1 | Go |
| Complexation | reaction in which ligands react with a metal atom to form a coordination complex. Source: WIkipedia | i | 3 | Go |
| Conia-ene reaction | intramolecular cyclization reaction between an enolizable carbonyl group and an unsaturated carbon-carbon bond, giving a cyclic product with a new carbon-carbon bond. Source: Wikipedia | i | 1 | Go |
| conjugate addition | A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). | i | 2 | Go |
| copper(I)-catalyzed azide-alkyne cycloaddition | A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer. | i | 310 | Go |
| Corey-Bakshi-Shibata reduction | Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine. | i | 24 | Go |
| Corey-Fuchs reaction | A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water. | i | 71 | Go |
| Corey-Fuchs terminal dihaloolefination | Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin often en route to an alkyne. Includes dichloro-olefination, includes ketones | i | 268 | Go |
| cross-coupling | A joining reaction where a carbon-carbon bond is formed between unlike moieties. | i | 7 | Go |
| Curtius rearrangement | A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen. The isocyanate may or may not be intercepted by a nitrogen or oxygen nucleophile | i | 128 | Go |
| cyanoacetic ester synthesis | Alkylation reaction of alkyl halides with compounds containing an alpha carbon flanked by a ester and a cyano group. Variation of malonic ester reaction. Source: March 0-96 | i | 50 | Go |
| cyclic alpha-haloketone Favorskii rearrangement | Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. | i | 3 | Go |
| cyclization | Formation of a ring in a molecule from a chain by formation of a new bond. | i | 16 | Go |
| cycloaddition | A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity. | i | 16 | Go |
| Cycloisomerisation | Intramolecular cyclization reaction, often catalyzed by a transition metal catalyst. Main classes intramoleculer Diels-Alder reactions and intramolecular Michael additions. Includes enyne cycloisomerization. Source: Wikipedia. | i | 158 | Go |
| Cyclopropanation | Any substitution reaction in which a cyclopropane ring is created. | i | 490 | Go |
| Davis oxidation | Formation of α-hydroxy carbonyl compounds (acyloins) from ketones or esters using oxaziridines. Source: Wikipedia. | i | 8 | Go |
| Deacetylation | The removal of a (protective) acetyl group, leaving an hydroxyl group. Source: Wikipedia | i | 4325 | Go |
| Dearomatization reaction | Any reaction removing aromaticity from a ring system, excluding Birch reduction. Source Wikipedia. | i | 1 | Go |
| decarboxylation | Breaking of a covalent bond between a molecule and a carboxy group. | i | 1305 | Go |
| dehalogenation | Breaking of a covalent bond between a substrate and a halo group. | i | 2 | Go |
| Dehydrogenation | Reaction involving the removal of hydrogen. Reverse of hydrogenation | i | 2 | Go |
| Dehydrohalogenation | dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. | i | 40 | Go |
| Delépine reaction | the of primary amines by reaction of benzyl or alkyl halides with hexamethylenetetramine followed by acid hydrolysis of the quaternary ammonium salt. Source: Wikipedia | i | 22 | Go |
| Demethylation at oxygen | Any reaction converting a methoxy group to an hydroxyl group with demethylation | i | 24728 | Go |
| deprotection reaction | A reaction in which a protecting group is modified by converting it into a functional group. | i | 2 | Go |
| Dess-Martin aldehyde oxidation | A Dess-Martin oxidation of a primary alcohol to an aldehyde. | i | 3556 | Go |
| Dess-Martin ketone oxidation | A Dess-Martin oxidation of a secondary alcohol to a ketone. | i | 1121 | Go |
| Dess-Martin oxidation | The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane. | i | 1 | Go |
| Diazo compound synthesis | Any reaction converting a methylene (CH2) group to a diazo (C=N=N) group. | i | 138 | Go |
| diazotisation | A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt. | i | 60 | Go |
| Dieckmann cyclisation | An intramolecular cyclisation of a diester to give a cyclic beta-ketoester. | i | 99 | Go |
| Diels-Alder reaction | A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound. | i | 41 | Go |
| Difluoromethoxylation and trifluoromethoxylation | Any reaction introducing a difluoromethoxy group or a trifluoromethoxy group into a molecule. Both functional groups are relevant to medicinal chemistry | i | 2 | Go |
| difluoromethyl group addition | Addition of an difluoromethyl group at nitrogen, oxygen or carbon | i | 1427 | Go |
| Dihydroxylation | any organic reaction which converts an alkene to a vicinal diol | i | 101 | Go |
| Dioxole synthesis | Any synthesis forming a dioxole (5-membered ring containing 2 oxygen atoms). A 1,3-diol can be protected with acetone or dimethoxypropane to a 1,3-dioxole. Ethylene glycol can protected a ketone. Includes 6-membered dioxanes | i | 446 | Go |
| Directed ortho metalation | Variation of electrophilic aromatic substitution with observed selectivity of electrophiles for the ortho position of a functional group activated by an organolithium compound. Source: Wikipedia | i | 2 | Go |
| displacement reaction | Displacement can be a single displacement or a double displacement (switching of bonds between two chemical compounds, salt metathesis). Source: Wikipedia | i | 5 | Go |
| Disulfide synthesis | Any reaction that forms a disulfide bond (S-S) | i | 197 | Go |
| Doyle–Kirmse reaction | an organic reaction in which in the original scope an allyl sulfide reacts with trimethylsilyldiazomethane to form the homoallyl sulfide compound. Source: Wikipedia | i | 12 | Go |
| Duff reaction | Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions. | i | 59 | Go |
| Einhorn–Brunner reaction | the chemical reaction of imides with alkyl hydrazines to form an isomeric mixture of 1,2,4-triazoles. (Source: Wikipedia) | i | 7 | Go |
| Electrocyclic reaction | type of pericyclic rearrangement reaction with one pi bond converted into a sigma bond or the reverse reaction. Source: Wikipedia | i | 1 | Go |
| Electrophilic decarboxylative halogenation | A type of electrophilic aromatic substitution with a halogenation donor reagent accompanied by decarboxylation | i | 122 | Go |
| Electrophilic halogenation | Type of electrophilic substitution reaction, replacing a hydrogen atom for a halide, usually catalysed by a Lewis acid. | i | 23358 | Go |
| electrophilic methylation | Electrophilic methylations are commonly performed using electrophilic methyl sources such as iodomethane, dimethyl sulfate, dimethyl carbonate, or tetramethylammonium chloride (Source: Wikipedia) | i | 1933 | Go |
| elimination reaction | A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring. | i | 3848 | Go |
| enamine - imine tautomerization | tautomerization reaction of an enamine to an imine. For example as result of N-Boc deprotection | i | 241 | Go |
| Enamine synthesis | Acid-catalyzed nucleophilic reaction of a ketone or aldehyde containing an α-hydrogen with secondary amines to form an enamine. Source: Wikipedia | i | 68 | Go |
| Enders SAMP/RAMP hydrazone-alkylation reaction | an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries.(Source: Wikipedia) | i | 4 | Go |
| ene reaction | A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. | i | 7 | Go |
| Epoxide reduction | Reduction reaction of an epoxide to the corresponding alcohol. | i | 89 | Go |
| Epoxy-ring opening | Ring-openings reaction of an epoxide with N,S,O nucleophiles | i | 1065 | Go |
| Eschenmoser fragmentation | Any reaction converting α,β-epoxyketones with aryl sulfonylhydrazines to give alkynes and carbonyl compounds. Source: Wikipedia. | i | 1 | Go |
| ester condensation reaction | A condensation reaction that results in the production of an ester. | i | 7 | Go |
| ester hydrolysis | Acid or base catalysed hydrolysis of an ester into an carboxylic acid and an alcohol. Does not include common deprotection reaction of methyl, ethyl, t-butyl, benzyl esters. reaction of Reverse of Fischer–Speier esterification. | i | 5 | Go |
| ester reduction to aldehyde | An ester reduction where the product is the corresponding aldehyde. | i | 909 | Go |
| ester reduction to an alcohol | A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced. Reduction to aldehyde not included | i | 14002 | Go |
| ethyl ester deprotection | A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid. | i | 22779 | Go |
| Evans−Tishchenko reduction | is the diastereoselective reduction of β-hydroxy ketones to the corresponding 1,3-anti diol monoesters. The reaction employs a Lewis acid, often samarium iodide, and an aldehyde. | i | 1 | Go |
| extrusion reaction | A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. | i | 6 | Go |
| Favorskii reaction | A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone | i | 77 | Go |
| Favorskii rearrangement | Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. | i | 1 | Go |
| Feist-Bénary synthesis | Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan. | i | 300 | Go |
| Ferrier rearrangement | The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound. | i | 3 | Go |
| Fiesselmann thiophene synthesis | allows for the generation of 3-hydroxy-2-thiophenecarboxylic acid derivatives from α,β-acetylenic esters with thioglycolic acid and its derivatives under the presence of a base | i | 2 | Go |
| Fischer indole synthesis | Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole. | i | 440 | Go |
| Fischer-Speier esterification | The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst. | i | 12917 | Go |
| Fleming-Tamao oxidation | The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid. | i | 3 | Go |
| Formamide dehydration to isonitrile | Formamide dehydration to isonitrile to form an isonitrile (CNC), usual reagents POCl3 or Burgess reagent | i | 59 | Go |
| formylation | Formation of a covalent bond between a substrate and a formyl group. | i | 84 | Go |
| Free amine formation | Reaction with base to a free amine from an ammonium salt with acids (HCl, carboxylic acid). (Source: Wikipedia) | i | 4 | Go |
| Free carboxylic acid formation | Conversion of any carboxylate salt to a free carboxylic acid | i | 1 | Go |
| Friedel-Crafts acylation | A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid. | i | 1093 | Go |
| Friedel-Crafts alkylation | A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid. | i | 279 | Go |
| Friedel-Crafts reaction | A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. | i | 6 | Go |
| functional group oxidation | A functional group modification reaction where a functional group is oxidised. | i | 3 | Go |
| functional group reduction | A functional group modification reaction where a functional group is reduced. | i | 1 | Go |
| Ganem oxidation | Conversion of alkyl halides to aldehydes with specific use of trialkylamine N-oxidess. For reaction with DMSO see Kornblum oxidation. Source: Wikipedia. | i | 2 | Go |
| Giese reaction | hydroalkylation process by the addition of nucleophilic radicals to electron-poor olefins. | i | 3 | Go |
| Giese-Baran cyclization | i | 2 | Go | |
| Grieco elimination | Elimination reaction of an aliphatic primary alcohol through a selenide to a terminal alkene. (Wikipedia) | i | 12 | Go |
| Grignard reaction | A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone. | i | 5302 | Go |
| Groebke–Blackburn–Bienaymé reaction | GBBR reaction, synthesis of a fused imidazole based on a multicomponent reaction of an aldehyde, isocyanide and amidine | i | 1 | Go |
| Guanylation | Addition of an amidine to an amine forming a guanidine, relevant to peptide synthesis | i | 106 | Go |
| Hajos–Parrish–Eder–Sauer–Wiechert reaction | Asymmetric aldol reaction with organocatalyst. Includes Barbas-List modifications. | i | 2 | Go |
| Haloform reaction | Conversion of methyl ketones to carboxylic acids, esters or amides via the perhalogenated intermediate. | i | 134 | Go |
| Halogen dance | Rearrangement of polyhaloaryls with strong base. March 1-45 | i | 2 | Go |
| halogenation | Formation of a covalent bond between a substrate and a halo group. | i | 30 | Go |
| Halogenation of 2-hydroxy-N-heterocycles | Conversion of 2-hydroxypyridines to 2-halopyridines with reagents such as POCl3 | i | 2358 | Go |
| Hauser-Kraus annulation | an anthraquinone forming reaction from a fused lactone and an alkene. | i | 1 | Go |
| Heck reaction | A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific. | i | 166 | Go |
| Heck-type reaction | A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin. | i | 1 | Go |
| Hell-Volhard-Zelinsky reaction | An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid. | i | 26 | Go |
| Henry reaction | A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane. | i | 12 | Go |
| hetero-Diels-Alder reaction | A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound. | i | 3 | Go |
| heteroaryl reduction to saturated heterocycle | A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. | i | 2060 | Go |
| Hofmann reaction | Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement | i | 6 | Go |
| Homologation reaction | any reaction converting a reactant into the next member of a homologous series for example extension of a chain by a methylene group. Source: Wikipedia | i | 1 | Go |
| homolytic aromatic substitution | Aromatic substitution involving radical species (HAS) | i | 1 | Go |
| Horner-Wadsworth-Emmons reaction | A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin. | i | 924 | Go |
| Hunsdiecker reaction | The decarboxylation of silver carboxylates with halogens to give organic halides. | i | 2 | Go |
| Hydrazine synthesis from amines | Reaction of an amine with sodium nitrite and a reducing agent | i | 373 | Go |
| hydroamination | The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine. | i | 890 | Go |
| hydroboration | The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon. | i | 41 | Go |
| hydroboration-oxidation | The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol. | i | 1113 | Go |
| Hydrogen atom transfer (HAT) | chemical reaction where a hydrogen free radical is removed from a substrate to another molecule. Source: Wikipedia | i | 3 | Go |
| hydrogenation | A reduction process that involves addition of hydrogen atoms across a double bond. | i | 11368 | Go |
| Hydrogenolysis | A reaction in which a carbon–carbon or carbon–heteroatom single bond is cleaved or undergoes lysis (breakdown) by hydrogen (source: Wikipedia). | i | 597 | Go |
| Hydrolysis of enol ethers and acetals | Hydrolysis reaction (acidic) of enol ethers or acetals to aldehydes and ketones. Source: March 0-7 | i | 1043 | Go |
| hydrostannylation | The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up. | i | 39 | Go |
| hydroxy group deprotection | A deprotection reaction where the reactive centre is an oxygen atom. | i | 18502 | Go |
| hydroxyl group protection | A protection reaction where the reactive centre is a hydroxyl oxygen atom. | i | 662 | Go |
| Hydroxylation | Any reaction adding a hydroxy group to a substrate. Includes allylic oxidation. Source: Wikipedia | i | 55 | Go |
| hydrozirconation | The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl. | i | 1 | Go |
| imidazole synthesis | A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants. | i | 4091 | Go |
| Imidazopyridine synthesis | Any reaction forming a imidazopyridine from a compound containing at least a primary amine group and a compound containing at least a carbonyl group | i | 1446 | Go |
| imide ring synthesis | Any ring-forming reaction involving the completion of a imide unit | i | 513 | Go |
| imide ring synthesis by amine and anhydride condensation | Any reaction between an amine and an anhydride forming an imide | i | 667 | Go |
| indazole synthesis | A planned reaction in which one of the products contains an indazole system that was not in any of the reactants. | i | 1 | Go |
| Intramolecular condensation imidazoline | Any condensation reaction that creates a imidazoline ring from a linear chain | i | 70 | Go |
| Intramolecular condensation thiazoline | Any condensation reaction that creates a thiazoline ring from a linear chain | i | 40 | Go |
| Intramolecular ester synthesis | Intramolecular formation of a cyclic ester from a hydroxycarboxylic acid | i | 441 | Go |
| Intramolecular imidazole synthesis | Any intramolecular reaction forming a new imidazole ring system | i | 1222 | Go |
| intramolecular Prins reaction | A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid. | i | 7 | Go |
| Intramolecular pyrimidine synthesis | Any intramolecular reaction forming an pyrimidine ring, may have oxo substituents, includes arene-fused quinazolines | i | 1032 | Go |
| inverse electron-demand Diels–Alder reaction | IEDDA, a cycloaddition between an electron-rich dienophile and an electron-poor diene. Source: Wikipedia | i | 1 | Go |
| iodo Heck reaction | A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. | i | 198 | Go |
| iodo Sonogashira coupling | A Sonogashira coupling where the aryl halide is an aryl iodide. | i | 1862 | Go |
| iodo Suzuki coupling | A Suzuki coupling where the halide is an iodide. | i | 5529 | Go |
| Isocyanate synthesis | Isocyanate synthesis (R=N=C=O) from amines and amides with phosgene. (Source: Wikipedia) | i | 193 | Go |
| Isocyanide synthesis | Isocyanide synthesis from formamide dehydration | i | 1 | Go |
| isomerization reaction | ANy reaction involving an isomerization, for example cis-trans isomerization | i | 4 | Go |
| Isoxazole synthesis | Any reaction forming a 5-membered aromatic isoxazole (NOCCC) ring system. | i | 333 | Go |
| Johnson-Claisen rearrangement | The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester. | i | 1 | Go |
| Johnson-Corey-Chaykovsky aziridine synthesis | Reaction of a sulfur ylide with an imine to produce an aziridine. | i | 4 | Go |
| Johnson-Corey-Chaykovsky cyclopropane synthesis | Reaction of a sulfur ylide with an olefin to produce a cyclopropane. | i | 450 | Go |
| Johnson-Corey-Chaykovsky epoxide synthesis | Reaction of a sulfur ylide with a ketone to produce an epoxide. | i | 349 | Go |
| Jones oxidation | An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. | i | 1216 | Go |
| Julia-Kocienski olefination | A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene. | i | 2 | Go |
| Keck asymmetric allylation | Enantioselective nucleophilic addition of an allyl group to an aldehyde. Source: Wikipedia | i | 2 | Go |
| keto to enol ether transformation | Conversion of an ketone or aldehyde to a enol ether. May be accompanied by secondary etherfication or esterification | i | 981 | Go |
| Ketone alpha-hydroxylation | Acyloin synthesis by hydroxylation of the alpha position of a ketone, for example with oxaziridines. Source: Wikipedia. | i | 93 | Go |
| Ketone halogenation | Ketones can be halogenated at the alpha position with bromine, chlorine or iodine to form a haloketone, also possible with aldehydes. (Source: March 2-4) | i | 2878 | Go |
| ketone reduction | A reduction process where a ketone is reduced to a secondary alcohol. | i | 8063 | Go |
| Knoevenagel condensation | A carbon-carbon coupling reaction of an aldehyde and a methylene compound. | i | 6759 | Go |
| Knoevenagel condensation, Doebner modification | A carbon-carbon coupling reaction of an aldehyde and an carboxylic acid, using pyridine as a base. | i | 56 | Go |
| Knorr pyrazole synthesis | Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. | i | 288 | Go |
| Kolbe electrolysis | The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer. | i | 1 | Go |
| Kornblum oxidation | Conversion of alkyl halides and alkyl tosyl compounds with DMSO into carbonyl-group containing compounds. Source: Wikipedia. | i | 9 | Go |
| Krapcho decarboxylation | Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system. | i | 1 | Go |
| Krische allylation | Enantioselective addition reaction of an allyl group to an aldehyde or an alcohol, resulting in a secondary homoallylic alcohol. Source: Wikipedia | i | 1 | Go |
| Kulinkovich reaction | Type of cyclopropanation by reaction of ester with dialkyldialkoxytitanium reagent generated from a Grignard reagent. Source: Wikipedia | i | 112 | Go |
| Kulinkovich reaction, Bertus-Szymoniak variation | Type of Kulinkovich reaction with a nitrile as substrate forming an amine substituted cyclopropane. Source: Wikipedia | i | 149 | Go |
| Kulinkovich reaction, De Meijere variation | Type of Kulinkovich reaction with an amide as substrate forming an non-primary amine substituted cyclopropane. Source: Wikipedia | i | 22 | Go |
| Kumada coupling | A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst. | i | 1 | Go |
| Lactam forming reaction | Any intramolecular reaction forming a lactam (cyclic amide) 5,6-membered ring. Source: WIkipedia | i | 5438 | Go |
| Lactone forming reaction | Any reaction forming a lactone, for example intramolecular esterification | i | 76 | Go |
| Larock indole synthesis | Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. | i | 3 | Go |
| Lemieux-Johnson oxidation | A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone. | i | 425 | Go |
| Ley oxidation | The use of Tetrapropylammonium perruthenate in the oxidation of a primary alcohol to an aldehyde. | i | 158 | Go |
| Liebeskind-Srogl coupling | A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst. | i | 1 | Go |
| Lithiation | Metalation with organolithium reagents, also known aslithium-hydrogen exchange,achieved when an organolithium reagent, most commonly an alkyllithium, abstracts a proton and forms a new organolithium species. Source: Wikipedia | i | 10 | Go |
| Luche reduction | The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride. | i | 6 | Go |
| malonic ester synthesis | A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl or aryl halide, to give a substituted acetic acid. The base/RX treatment can be repeated to give a disubstituted product. | i | 648 | Go |
| Mannich reaction | A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound. | i | 5 | Go |
| Matteson Homologation | Synthesis of alpha-halo boronic ester from an boronic ester and a dihalomethyl compound | i | 17 | Go |
| McLoughlin-Thrower reaction | Coupling reaction and trifluoromethylation using iodofluoroalkanes, iodoaromatic compounds and copper. Source: Wikipedia | i | 101 | Go |
| McMurry reaction | Coupling eaction of ketones or aldehydes to an alkene using a titanium reagent and an reducing agent. Source: Wikipedia | i | 29 | Go |
| Meerwein-Ponndorf-Verley reduction | A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047). | i | 1 | Go |
| Meerwein-Ponndorf-Verley reduction of a ketone | Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol. | i | 11 | Go |
| Meerwein-Ponndorf-Verley reduction of an aldehyde | Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol. | i | 1 | Go |
| Meinwald Rearrangement | Stereoselective rearrangement of an epoxide to a cyclic ketone. | i | 1 | Go |
| Menshutkin reaction | The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt. | i | 954 | Go |
| methyl ester deprotection | A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid. | i | 28501 | Go |
| Methyl ketone oxidation | Methyl ketone oxidation to an alpha keto-carboxylic acid, reagents selenium dioxide, potassium permanganate. | i | 27 | Go |
| Michael addition | A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). | i | 48 | Go |
| MIDA boronate synthesis | Synthesis of boronate esters for Suzuki-Miyaura cross-coupling reaction stabilized with N-methyliminodiacetic acid (MIDA) | i | 3 | Go |
| Milas dihydroxylation | Conversion of alkene to vicinal diol with use of stoichiometric amount of peroxide. | i | 39 | Go |
| Minisci reaction | Nucleophilic radical substitution adding an alkyl group to an electron-deficient heterocycle. Source: Wikipedia | i | 42 | Go |
| Mitsunobu reaction | A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted. | i | 7711 | Go |
| Miyaura borylation | A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions | i | 9565 | Go |
| molecular ring formation objective | A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants. | i | 3 | Go |
| Mukaiyama aldol addition | An aldol addition between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound. | i | 8 | Go |
| Mukaiyama aldol condensation | An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound. | i | 1 | Go |
| Mukaiyama hydration | The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen | i | 32 | Go |
| N-acylation to amide | An acylation reaction where a nitrogen atom is acylated to form an amide. Not included: BOC protection reactants. Reagents include: trifluoroacetic anhydride, phthalic anhydride | i | 1511 | Go |
| N-acylation to carbamate | An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. | i | 478 | Go |
| N-acylation to urea | An acylation reaction where a nitrogen atom is acylated to form a urea. | i | 40 | Go |
| N-alkylation | Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group. | i | 40536 | Go |
| N-halogenation | Any halogenation at a nitrogen position forming a N-Hal bond Hal = Br, Cl, F, I | i | 74 | Go |
| N-hydro-C-cyano-addition | Any Reaction with cyanide ion adding to imines, Schiff bases , hydrazine's and similar compounds (March 3rd 6.51) | i | 42 | Go |
| N-nitration | Formation of a covalent bond between a nitrogen atom in a substrate and a nitro group. | i | 13 | Go |
| N-oxide reduction | Reduction of an N-oxide to an amine. Includes pyridine N-oxide deoxygenation | i | 21 | Go |
| N-sulfinyl imine hydrolysis | Conversion of an N-sulfinyl imine to a terminal imine in acidic hydrolysis | i | 22 | Go |
| NAS at N-heterocycles | Nucleophilic aromatic substitution (NAS) at N-heterocycles (pyridine, pyrimidine) with nitrogen, oxygen or sulfur nucleophiles. Metal free. | i | 37886 | Go |
| NAS with O-nucleophiles@heterocycles | a nucleophilic substitution reaction with oxygen nucleophiles and a heterocycle (not requiring a leaving group). | i | 22 | Go |
| NAS with S-nucleophiles@heterocycles | a nucleophilic substitution reaction with sulfur nucleophiles and a heterocycle (not requiring a leaving group). | i | 83 | Go |
| Nazarov cyclisation | The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone. | i | 1 | Go |
| Nef reaction | The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively. | i | 7 | Go |
| Negishi coupling | A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel. | i | 199 | Go |
| Nitrene reaction | Reaction involving a nitrene reactive intermedaiate | i | 2 | Go |
| nitrile alcoholysis | An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. | i | 2 | Go |
| nitrile hydrolysis | Hydrolysis reaction of an nitrile to an carboxylic acid. Acid or base catalysed via de intermediate amide. (March 6.5) | i | 1843 | Go |
| Nitrile hydrolysis to acetamide | Nitrile hydrolysis to acetamide | i | 3104 | Go |
| Nitrile reduction to aldehyde | Any reduction converting a nitrile to the corresponding aldehyde | i | 694 | Go |
| nitrile reduction to amine | A reduction where a nitrile is replaced by an amine function. | i | 3883 | Go |
| nitro reduction to amine | A reduction reaction where a nitro group is reduced to an amino group. | i | 29747 | Go |
| nitro-Michael reaction | A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound. | i | 5 | Go |
| Nitrogen phosphorus bond formation | Formation of any new bond between nitrogen and phosphorus | i | 27 | Go |
| Norrish reaction | is the photochemical cleavage or homolysis of aldehydes and ketones into two free radical intermediates (α-scission). (Source Wikipedia) | i | 1 | Go |
| Noyori asymmetric hydrogenation, alkene | The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst. | i | 4 | Go |
| Noyori asymmetric hydrogenation, carbonyl | The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst. | i | 3 | Go |
| Nozaki-Hiyama-Kishi reaction | A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel. | i | 10 | Go |
| Nucleophilc substitution at dithioimines | Formal substitution by a nitrogen or oxygen nucleophile of the thio group in a dithioimine for example dimethyl N-cyanodithioiminocarbonate. Also includes related carbonimidate N=C(O)O substrates | i | 137 | Go |
| Nucleophilic acyl substitution with C-nucleophiles | Nucleophilic acyl substitution reaction between a compound containing an acidic carbon-hydrogen bond forming a C-nucleophile with a compound containing an acyl group containing a leaving group. | i | 38 | Go |
| Nucleophilic addition | an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. (Source: Wikipedia) | i | 1795 | Go |
| Nucleophilic aliphatic substitution with C-nucleophiles | Nucleophilic aliphatic substitution reaction between a compound containing an acidic carbon-hydrogen bond forming a C-nucleophile with a compound containing an aliphatic carbon atom containing a leaving group. | i | 714 | Go |
| nucleophilic aromatic substitution | a substitution reaction in which a N or O nucleophile displaces a good leaving group, such as a halide, on an electron deficient aromatic ring. Nucleophile can also be Sn,F (source: Wikipedia) | i | 46587 | Go |
| nucleophilic aromatic substitution with S-nucleophiles | a substitution reaction in which an sulfur nucleophile displaces a good leaving group, such as a halide, on an electron deficient aromatic ring. | i | 236 | Go |
| Nucleophilic Vinylic Substitution (SNV) | Reaction where a nucleophile displaces a leaving group at a vinylic sp2 carbon atom | i | 8 | Go |
| O-acylation to ester | An O-acylation reaction where an oxygen centre is acylated to result in an ester. | i | 3523 | Go |
| O-nitration | Formation of a covalent bond between an oxygen atom in a substrate and a nitro group. | i | 36 | Go |
| O-silyl deprotection | Reaction involving the removal of a silyl protective group, e.g. TMS, TES,TBS, TIPS, TBDPS | i | 7614 | Go |
| O-silylation | Formation of a covalent bond between an oxygen atom in a substrate and a silyl group. | i | 12 | Go |
| Oppenauer oxidation | An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide. | i | 4 | Go |
| Organocopper incorporating reaction | Any reaction introducing an organocopper bond in a substrate | i | 1 | Go |
| Organogermanium incorporating reaction | Any reaction introducing an organogermanium bond in a substrate | i | 4 | Go |
| Organomagnesium reaction | Any reaction forming a magnesium to carbon chemical bond. Includes organomagnesium halides for use in Grignard reactions | i | 56 | Go |
| Organomercury incorporating reaction | Any reaction introducing an organomercury bond in a substrate | i | 2 | Go |
| organometallic methylene-de-oxo-substitution | Any organometallic reaction converting a ketone to the corresponding methylene, reagents Tebbe, Nysted, Petasis | i | 13 | Go |
| organometallic reaction | Any reaction involving a metal and an organic residue | i | 3 | Go |
| Organophosphonium compound synthesis | Synthesis of phosphonium salts from phosphines and alkyl halides. Usually step preceding a Witting reaction | i | 526 | Go |
| Organosilicon incorporating reaction | Any reaction introducing an organosilicon bond in a substrate | i | 2 | Go |
| Organotin incorporating reaction | Any reaction introducing an organotin bond in a substrate | i | 2 | Go |
| Organozinc incorporating reaction | Any reaction introducing an organozinc bond in a substrate | i | 5 | Go |
| oxa-Diels-Alder reaction | A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound. | i | 23 | Go |
| Oxazole synthesis | Any reaction forming a 5-membered aromatic oxazole (NCOCC) ring system. | i | 88 | Go |
| Oxazoline synthesis | Any reaction forming an oxazoline, substrates: beta-amino-alcohols, nitriles and aldehydes | i | 190 | Go |
| oxidation | The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate. | i | 15 | Go |
| oxidation at sulfur | An oxidation process where the oxidation state of at least one sulfur atom increases. | i | 7592 | Go |
| oxy-Cope rearrangement | A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound. | i | 3 | Go |
| P-alkylation | The formation of a covalent bond between a phosphorus atom and an alkyl group. | i | 14 | Go |
| Paal-Knorr furan synthesis | The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan. | i | 22 | Go |
| Paal-Knorr pyrrole synthesis | The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole. | i | 484 | Go |
| Paal-Knorr thiophene synthesis | The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene. | i | 23 | Go |
| palladium-catalysed carbon-carbon coupling reaction | A carbon-carbon coupling reaction that is catalysed by a palladium atom. | i | 17 | Go |
| Parikh–Doering oxidation | an oxidation reaction that transforms primary and secondary alcohols into aldehydes and ketones, respectively. The procedure uses dimethyl sulfoxide (DMSO) as the oxidant and the solvent, activated by the sulfur trioxide pyridine complex (SO3•C5H5N) in the presence of triethylamine or diisopropylethylamine as base (source: Wikipedia). | i | 16 | Go |
| Passerini reaction | The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide. | i | 3 | Go |
| Pauson-Khand reaction | A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone. | i | 1 | Go |
| Pechmann pyrazole synthesis | Reaction of an organic diazo compound with an acetylene to yield a pyrazole. | i | 72 | Go |
| Pellizzari reaction | the organic reaction of an amide and a hydrazide to form a 1,2,4-triazole. (Source: Wikipedia) | i | 1 | Go |
| Peptide coupling reaction | A reaction between an carboxylic acid or ester and an amine forming an amide, often aided by dedicated coupling reagents | i | 89701 | Go |
| Peterson olefination | A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base. | i | 10 | Go |
| Pfitzinger reaction | The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid. | i | 101 | Go |
| Phillips benzimidazole synthesis | Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole. | i | 553 | Go |
| phthalimide deprotection | Conversion of a phthalimide into the corresponding primary amine. | i | 1497 | Go |
| phthalimide protection | Protection of a primary amino group by reaction with phthalic anhydride. | i | 351 | Go |
| Pictet-Spengler reaction | A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline. | i | 2 | Go |
| pinacol rearrangement | A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid. | i | 1 | Go |
| Pinner pyrimidine synthesis | Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine. | i | 2 | Go |
| Pinner reaction | A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. | i | 463 | Go |
| Pinner triazine synthesis | Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia. | i | 7 | Go |
| Pinnick oxidation | oxidation of an aldehyde to the corresponding carboxylic acid using sodium chlorite. Source: Wikipedia | i | 590 | Go |
| Prilezhaev epoxidation | Epoxidation of an alkene by reaction with a peroxy acid. | i | 471 | Go |
| primary alcohol oxidation to aldehyde | An oxidation process where a primary alcohol is transformed into an aldehyde. | i | 3925 | Go |
| Primary amide synthesis | Primary amide synthesis from a carboxylic acid and ammonia. | i | 3800 | Go |
| Prins reaction | A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid. | i | 2 | Go |
| Propargylic nucleophilic addition to an aldehyde | Nucleophilic addition reaction subset with an alkyne reactant reacting with an aldehyde forming a propargylic alcohol | i | 196 | Go |
| pyrazole synthesis | A reaction in which the intended product is a pyrazole that was not present in any of the reactants. | i | 4506 | Go |
| Pyrazolopyrimidine synthesis | Any reaction forming a pyrazolopyrimidine from a compound containing at least a primary amine group and a compound containing at least a carbonyl group, tautomers included | i | 1018 | Go |
| pyridine synthesis | Ring formation reaction where the intended product is a pyridine. | i | 3 | Go |
| Pyrrole protected amine deprotection | Aromatic amines can be liberated by removal of a protecting 2,5-dimethylpyrrole group. Reverse of pyrrole synthesis with acetonylacetone. | i | 139 | Go |
| pyrrole reduction | Partial or complete reduction of a pyrrole to a dihydropyrrole or a pyrrolidine with a reducing agent | i | 668 | Go |
| pyrrole synthesis | A reaction in which the intended product is a pyrrole that was not present in any of the reactants. | i | 152 | Go |
| Quaternary carbon center synthesis | Any reaction adding a queternary carbon center to the scaffold | i | 124 | Go |
| Racemization | Reaction of an optically active compound into a racemic form. Source: Wikipedia | i | 2 | Go |
| Radical reaction | Any reaction involving radical reactive intermediates | i | 5 | Go |
| rearrangement step | A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another. | i | 2 | Go |
| reduction | The complete transfer of one or more electrons to a molecular entity. | i | 4 | Go |
| Reduction of azides, isocyanates to amines | Azides can be reduced to primary amines, isocyanates and isothiocyanate to methyl amines (March 9.15) | i | 3 | Go |
| reductive amination | A functional group modification where a carbonyl oxygen is replaced by an amine. | i | 23748 | Go |
| reductive dimerization | Any coupling reaction and dimerization of two aryl or alkenyl halides to form a new unsaturated carbon-carbon bond, catalysed by metals such as zinc and copper | i | 1 | Go |
| reductive imination | A functional group modification where a carbonyl oxygen is replaced by an imine. | i | 1 | Go |
| Reformatsky reaction | A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester. | i | 1 | Go |
| Rieche formylation | Formylation reaction with dichloromethyl methyl ether and titanium tetrachloride. Source: Wikipedia | i | 6 | Go |
| Riley oxidation | is a selenium dioxide-mediated oxidation of methylene groups adjacent to carbonyls (source: Wikipedia). | i | 103 | Go |
| ring breaking | A planned reaction step in which the product has fewer rings than the reactants. | i | 2 | Go |
| ring contraction | A planned reaction step in which an existing ring is reduced in size. | i | 3 | Go |
| ring expansion | A reaction in which an existing ring is increased in size. | i | 7 | Go |
| ring formation reaction step | A planned reaction step where the product contains a ring that was not in any of the reactants. | i | 13 | Go |
| ring rearrangement | A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. | i | 1 | Go |
| ring-closing metathesis | A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. | i | 356 | Go |
| ring-opening metathesis | A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. | i | 2 | Go |
| ring-opening reaction general | Any reaction in which a ring structure is opened. Metathesis excluded. | i | 5 | Go |
| Robinson–Gabriel synthesis | an organic reaction in which a 2-acylamino-ketone reacts intramolecularly followed by a dehydration to give an oxazole (Wikipedia). | i | 198 | Go |
| Rosenmund-von Braun reaction | A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile. | i | 5096 | Go |
| Rubottom oxidation | The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product | i | 1 | Go |
| S-alkylation | Alkylation reaction at sulfur forming thio ethers or sulfonium salts. Includes thioketone to thio-enone conversion | i | 913 | Go |
| Sakurai reaction, acetal or ketal | A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether. | i | 3 | Go |
| Sandmeyer bromination | An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide. | i | 1047 | Go |
| Sandmeyer chlorination | An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride. | i | 487 | Go |
| Sandmeyer fluorination | An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride. | i | 7 | Go |
| Sandmeyer iodination | An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide. | i | 13 | Go |
| Sandmeyer reaction | An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide. | i | 1 | Go |
| Sandmeyer reaction, copper free | An aromatic substitution reaction where an aryl diazonium salt or amine reacts with a halogen source to form an aromatic halide or pseudohalide. | i | 134 | Go |
| Schmidt Glycosylation | the coupling of a glycosyl donor to a glycosyl acceptor forming a glycoside using trichloroacetimidates. | i | 1 | Go |
| Schmidt rearrangement, carboxylic acid | The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom. | i | 147 | Go |
| Schotten-Baumann reaction | The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase. Type of acylation. | i | 37860 | Go |
| secondary alcohol oxidation to ketone | An oxidation process where a secondary alcohol is transformed into a ketone. | i | 549 | Go |
| secondary, non-terminal alkene oxidation to aldehydes | An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate. | i | 114 | Go |
| Selenium incorporating reaction | Any reaction introducing an organoselenium bond into a substrate | i | 29 | Go |
| Selenoxide elimination | is a method for the chemical synthesis of alkenes from selenoxides.Source: Wikipedia | i | 31 | Go |
| semipinacol rearrangement | A rearrangement of a 1,2-diol | i | 1 | Go |
| Seyferth-Gilbert aldehyde homologation | Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. | i | 15 | Go |
| Seyferth-Gilbert homologation | Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. | i | 79 | Go |
| Seyferth-Gilbert homologation, Bestmann modification | Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction of the Ohira-Bestmann reagent with methanol and potassium carbonate. | i | 333 | Go |
| Shapiro reaction | The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin. | i | 2 | Go |
| Sharpless asymmetric dihydroxylation | The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix. | i | 135 | Go |
| Sharpless asymmetric epoxidation | The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate. | i | 5 | Go |
| silyl protection | A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether. | i | 7163 | Go |
| Simmons-Smith reaction | A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane. | i | 181 | Go |
| Skraup reaction | A condensation between an aromatic amine and glycerol to give a quinoline. | i | 86 | Go |
| Sommelet reaction | The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine. | i | 13 | Go |
| Sonogashira coupling | A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium. | i | 3858 | Go |
| Staudinger reaction | A joining of an organic azide and a tertiary phosphine to give a phosphazo compound. Includes traceless modification | i | 63 | Go |
| Staudinger synthesis | Reaction of an imine and an ketene to form a beta-lactam via a [2+2] cycloaddition. Source: Wikipedia | i | 1 | Go |
| Stetter reaction | 1,4-addition reaction with a nucleophilic catalyst | i | 109 | Go |
| Still-Gennari modification | A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins. | i | 12 | Go |
| Stille coupling | A carbon-carbon coupling reaction where a stannane (organotin cmp.) reacts with an organohalide or organotriflate. | i | 5624 | Go |
| Stork enamine alkylation | Any reaction involving an enamine and a Michael acceptor. Source: Wikipedia | i | 85 | Go |
| Strecker reaction | An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid. | i | 163 | Go |
| Sulfinamide hydrolysis | Conversion of a sulfinamide to the free amine. | i | 1561 | Go |
| Sulfonamide arylation | Sulfonamide (RSO2NH2) arylation with haloarenes to substituted sulfonamides in nucleophilic aromatic substitution | i | 269 | Go |
| Sulfonamide synthesis from sulfonylchlorides | Formation of an sulfonamide from an amine and a sulfonyl chloride. Protection reactions excluded | i | 11840 | Go |
| Sulfonyl chloride synthesis | Any reaction forming a sulfonyl chloride (RSO2Cl) from a sulfonic acid (RSO3H) for example with phosphorous oxychloride or thionyl chloride. Also includes the other halides. | i | 442 | Go |
| Sulfur dioxide extrusion | any reaction in which sulfur dioxide is extruded from a ring system (March 7-51) | i | 6 | Go |
| Suzuki-Miyaura coupling | The coupling of two unsaturated halides, triflates or sulfonates with a boron-based reagent, catalysed by a palladium(0) complex. | i | 1656 | Go |
| Swern oxidation | The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols. | i | 1643 | Go |
| Takai olefination | Reaction of an aldehyde with a diorganochromium compound to form an alkene. Source: Wikipedia | i | 7 | Go |
| tert-butyl carboxylic acid protection | A carboxy group protection where the product is a tert-butyl ester. | i | 906 | Go |
| tert-butyl ester deprotection | A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid. | i | 8793 | Go |
| Tetrazole synthesis | Any reaction forming a tetrazole ring. Includes reaction of a nitrile with an azide. | i | 419 | Go |
| Thiazole synthesis | Any thiazole ring form reaction. | i | 2494 | Go |
| Thioamide reduction | Any reaction reducing a thioamide NHC=S to the corresponding amine. The thioamide is usually derived from the corresponding amide (see Carbonyl thiation). | i | 13 | Go |
| Thioamide synthesis | Any reaction forming a thioamide C(=S)N. Also see carbonyl thiation. | i | 14 | Go |
| Thiocarbonate synthesis | i | 3 | Go | |
| Thioester synthesis | Any reaction forming an thioester for example reaction of a thioalcohol with an acyl halide. Source: WIkipedia | i | 49 | Go |
| thioketone compound to imine conversion | A functional group modification where a thioketone compound is converted to an imine. With an α-carbonyl proton present the reaction product is an enamine. | i | 374 | Go |
| Thiophene synthesis | Any thiophene ring forming reaction | i | 3 | Go |
| Transesterification | Alcoholysis reaction of an ester. Equilibrium reaction acid / base catalyzed (March 0-25) | i | 80 | Go |
| Transfer hydrogenation | Transfer hydrogenation is the addition of hydrogen to a molecule from a source other than gaseous hydrogen | i | 51 | Go |
| Transhydrocyanation | Cyanide transfer from acetone cyanohydrin to another acceptor with acetone as byproduct. Source: Wikipedia. | i | 38 | Go |
| transition-metal catalysed cyanation of aryl halides | Type of coupling reaction with substrates aryl halides and dicyanozinc, catalysts based on Pd, Cu, Ni | i | 229 | Go |
| Trifluoromethylation | Any organic reaction that introduces a trifluoromethyl group in an organic compound. Source: Wikipedia | i | 845 | Go |
| triflyloxy Heck reaction | A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. | i | 21 | Go |
| triflyloxy Sonogashira coupling | A Sonogashira coupling where the role of the halide is played by a triflyloxy group. | i | 133 | Go |
| triflyloxy Suzuki coupling | A Suzuki coupling where the rule of the halide is played by a triflyloxy group. | i | 1710 | Go |
| Tsuji-Trost reaction | A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0). | i | 5 | Go |
| Ugi reaction | Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide. | i | 5 | Go |
| Ullmann condensation | A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound. | i | 1 | Go |
| Ullmann reaction | A carbon-carbon homocoupling reaction of an aryl halide mediated by copper. | i | 404 | Go |
| Upjohn dihydroxylation | an organic reaction which converts an alkene to a cis vicinal diol with N-methylmorpholine N-oxide as stoichiometric re-oxidant for osmium tetroxide. | i | 859 | Go |
| Urea synthesis | Synthesis of ureas and thioureas by addition of an amine to a isocyanate or isothiocyanate. (March 6-17) | i | 6135 | Go |
| Van Leusen reaction | is the reaction of a ketone with TosMIC leading to the formation of a nitrile. (Source Wikipedia) | i | 90 | Go |
| Vilsmeier-Haack reaction | A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde. | i | 31 | Go |
| Wacker-Tsuji oxidation | The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. | i | 1 | Go |
| Wagner–Meerwein rearrangement | A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon | i | 1 | Go |
| Weinreb amide synthesis | Weinreb amide synthesis leading up to Weinreb ketone synthesis | i | 37 | Go |
| Weinreb ketone synthesis | The conversion of an acid chloride with N,O-dimethylhydroxylamine to form a Weinreb–Nahm amide, and subsequent treatment with an organometallic reagent such as a Grignard reagent or organolithium reagent to form a ketone or with an reducing agent to an aldehyde. (Source Wikipedia) | i | 2049 | Go |
| Williamson ether synthesis | The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether. | i | 33133 | Go |
| Wittig homologization | A wittig reaction of an aldehyde with a specific phosphorane to extend a chain by one methylene group | i | 2 | Go |
| Wittig methylenation | A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene. | i | 17 | Go |
| Wittig reaction | A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene. | i | 4114 | Go |
| Wolff rearrangement | A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen. | i | 1 | Go |
| Wolff-Kishner reduction | The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base. | i | 357 | Go |
| Xanthate synthesis | Xanthate ROC(S)SR' synthesis from an alcohol, CS2 and methyl iodide, usually as a precursor for a Barton-McComby deoxygenation. Also includes synthesis of carbothioyloxy compounds. | i | 81 | Go |
| Yamaguchi esterification | The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent). | i | 13 | Go |
| Yamaguchi lactonisation | The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification. | i | 5 | Go |
| Zweifel olefination | Reaction of a vinyl borane with a base and a halogen to form a alkene. Transition-metal free alternative to Suzuki-Miyaura reaction | i | 9 | Go |
| [1,5]-sigmatropic rearrangement | A [1,5] sigma tropic shift involves the shift of 1 substituent (hydride, alkyl, or aryl) down 5 atoms of a π system. Source: Wikipedia | i | 2 | Go |
| [2+2+1] cycloaddition | A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products. | i | 2 | Go |
| [2+2+2] cycloaddition | Type of cycloaddition with three alkyne units forming a benzene ring. Als: alkyne cyclotrimerisation. | i | 3 | Go |
| [2+2] cycloaddition | A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products. | i | 10 | Go |
| [3+2] cycloaddition | A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products. | i | 3 | Go |
| [4+2] cycloaddition | A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products. | i | 2 | Go |
| [5+2+1] cycloaddition | A cycloaddition in which one participant contributes five electrons and the other participant contributes two electrons to the transformation of reactants to products. | i | 1 | Go |
| α,α-dihalogenation of carbonyl compounds | Dihalogenation of ketones at the alpha position forming a dihalo methylene group | i | 863 | Go |
classification based on Ontobee name reaction ontology