Overview of reaction types organic reaction database



Reaction name Description namespace Count
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 58 Go
Aliphatic nucleophilic substitution Reaction of a nucleophile for example a bromine anion with an aliphatic substrate with a good leaving group i 175 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 1 Go
Appel bromination Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine. i 1367 Go
Appel chlorination Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane. i 96 Go
Appel iodination Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane. i 183 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 1 Go
Benzyl alcohol reduction Reduction of an aromatic methyl alcohol group to a methyl group i 14 Go
Boc deprotection An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions. i 9366 Go
bromo Heck-type reaction A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin. i 645 Go
bromo Suzuki coupling A Suzuki coupling where the halide is a bromide. i 4697 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 4992 Go
carboxylic acid to primary alcohol reduction A carboxylic acid reduction where the product is the corresponding primary alcohol. i 1166 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 127 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 Suzuki coupling A Suzuki coupling where the halide is a chloride. i 1765 Go
cross-coupling A joining reaction where a carbon-carbon bond is formed between unlike moieties. i 1 Go
Dess-Martin aldehyde oxidation A Dess-Martin oxidation of a primary alcohol to an aldehyde. i 902 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
diazotisation A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt. i 1 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 1 Go
ester reduction to aldehyde An ester reduction where the product is the corresponding aldehyde. i 451 Go
ethyl ester deprotection A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid. i 1144 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
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
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 2474 Go
Hell-Volhard-Zelinsky reaction An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid. i 14 Go
Henry reaction A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane. i 1 Go
hydrogenation A reduction process that involves addition of hydrogen atoms across a double bond. i 1437 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 38 Go
hydroxy group deprotection A deprotection reaction where the reactive centre is an oxygen atom. i 876 Go
iodo Heck reaction A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. i 201 Go
iodo Suzuki coupling A Suzuki coupling where the halide is an iodide. i 1006 Go
Johnson-Corey-Chaykovsky epoxide synthesis Reaction of a sulfur ylide with a ketone to produce an epoxide. i 66 Go
ketone reduction A reduction process where a ketone is reduced to a secondary alcohol. i 2861 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 424 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 1 Go
methyl ester deprotection A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid. i 1551 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 1 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 1090 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 19 Go
nitro reduction to amine A reduction reaction where a nitro group is reduced to an amino group. i 14650 Go
Nucleophilic aromatic substitution at N-heterocycles Nucleophilic aromatic substitution at N-heterocycles (pyridine, pyrimidine) with N-nucleophiles or O-nucleophiles or S-nucleophiles i 4890 Go
Passerini reaction The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide. i 1 Go
Peptide coupling reaction A reaction between an carboxylic acid and an amine forming an amide, often aided by dedicated coupling reagents i 26206 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
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 1 Go
ring expansion A reaction in which an existing ring is increased in size. i 1 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
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. i 7706 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 117 Go
Seyferth-Gilbert-Bestmann homologation Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. i 3 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 56 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 1 Go
silyl protection A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether. i 713 Go
Stille coupling A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate. i 629 Go
Sulfur dioxide extrusion any reaction in which sulfur dioxide is extruded from a ring system (March 7-51) i 4 Go
tert-butyl ester deprotection A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid. i 467 Go
Transfer hydrogenation Transfer hydrogenation is the addition of hydrogen to a molecule from a source other than gaseous hydrogen i 44 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 Suzuki coupling A Suzuki coupling where the rule of the halide is played by a triflyloxy group. i 238 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 312 Go
Williamson ether synthesis The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether. i 12405 Go
Wittig reaction A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene. i 1370 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

classification based on Ontobee Name reaction ontology