Coupling Reactions
Castro-Stephens Coupling
Coupling of alkynyl cuprates and aryl halides.
Friedel-Crafts Acylation
Coupling of aryls and acyl halides with Lewis acid catalyst.
Friedel-Crafts Alkylation
Coupling of aryls and alkyl halides with Lewis acid catalyst.
Friedel-Crafts Arylation
Also known as: Scholl Reaction
Coupling of two substituted aryls with Lewis acid catalyst.
Gomberg Reaction
Also known as: Gomberg-Bachmann Reaction
Coupling of aryls and aryl diazonium salts in alkaline solution.
Heck Reaction
Coupling of alkyls and aryls with Pd catalyst.
Pschorr Reaction
Intramolecular coupling of aryls and aryl diazonium salts.
Note: Intramolecular variation of the Gomberg reaction.
Sonogashira Coupling
Coupling of terminal alkynes and aryl halides with Pd catalyst.
Stille Reaction
Coupling of alkyl halides and organotins with Pd catalyst.
Suzuki Reaction
Also known as: Suzuki-Miyaura Reaction
Coupling of arylboronic acids and aryl halides.
Ullmann Reaction
Coupling of two aryl halides with Lewis acid catalyst.
Wurtz Reaction
Coupling of two alkyl halides with sodium.
Nucleophilic Aliphatic Substitution Reactions
Bunte Salt Formation
Reaction between alkyl halides and disulfur trioxides (S2O32-) forming Bunte salts.
Finkelstein Reaction
Also known as: Halogen exchange reaction
Reaction between alkyl halides and halide salts resulting in halogen exchange.
Gabriel Synthesis
Reaction between alkyl halides and phthalimide salts forming phthalimides that are hydrolysed into primary amines.
Note: RNH3+ salts are usually formed and can be converted to the amine.
Ing-Manske Procedure
A variation of the Gabriel synthesis. In the second step, the phthalimide is heated with hydrazine to form the primary amine instead.
Menshutkin Reaction
Reaction between alkyl halides and tertiary amines forming quaternary ammonium salts.
Note: Similar reactions involving primary and secondary amines exist (alkylation of amines).
Meyers Synthesis
Three-step reaction forming aldehydes from oxazines.
Mitsunobu Reaction
Reaction between alkyl halides and carboxylates forming esters.
Note: Carboxylic acids are sometimes used as well.
Stork Enamine Reaction
Also known as: Stork enamine alkylation
Reaction between carbonyls and secondary amines forming α-alkylated products.
von Braun Reaction
Also known as: Cyanamide formation
Reaction between bromonitriles and tertiary amines forming cyanamides.
Williamson Ether Synthesis
Reaction between alkyl halides and alkoxide anions forming ethers.
Electrophilic Aliphatic Substitution Reactions
Haller-Bauer Reaction
Reaction between ketones and sodium amide resulting in the ketone being cleaved.
Hell-Volhard-Zelinsky Reaction
Reaction between molecular halides and carboxylic acids resulting in α-halogenation.
Note: Usually only Cl2 or Br2 is used.
Japp-Klingemann Reaction
Reaction between carbonyls and diazonium salts forming hydrazones at the α-position.
Regitz Diazo-Transfer Reaction
Reaction between activated aliphatics and tosyl azides forming diazo compounds.
Note: Rarely do unactivated carbonyl compounds react via this method.
Nucleophilic Aromatic Substitution Reactions
Bucherer Reaction
Reaction between naphthols and ammonia forming naphthamines.
Chichibabin Reaction
Reaction between pyridines and sodium amide resulting in amination.
Goldberg Reaction
Intramolecular reaction between aryl halides and sodium amide forming amines.
Hurtley Reaction
Reaction between aryl halides and carbons with active hydrogens resulting in arylation.
Note: Catalysis is performed by copper halides.
Meerwein Arylation
Reaction between activated alkenes and aryl diazonium salts resulting in arylation.
Rosenmund von Braun Reaction
Reaction between aryl halides and CuCN forming aryl nitriles.
Sommelet-Hauser Rearrangement
Reaction between benzylic quaternary ammonium salts and sodium amide resulting in rearrangement of the ammonium salt (not the carbon it is bonded to).
Smiles Rearrangement
Intramolecular reaction of nucleophilic substituents and activated aryls.
Note: A variation is the Truce-Smiles rearrangement where the nucleophile is a carbanion.
Ullmann Condensation
Also known as: Ullmann ether synthesis
Reaction between aryl halides and activated phenols forming diaryl ethers.
Note: Not to be confused with the Ullmann reaction.
von Richter Rearrangement
Reaction between nitrobenzenes and cyanide ions resulting in cine substitution of a carboxylic acid (hydrolysis is not involved).
Note: Cine substitution is where the substituent forms adjacent to the leaving group carbon.
Ziegler Alkylation
Reaction between aryls containing heteroatoms and alkyllithiums resulting in arylation.
Electrophilic Aromatic Substitution Reactions
Balz-Schiemann Reaction
Reaction between aryl diazonium salts and fluoroborates forming fluorobenzenes.
Fischer-Hepp Rearrangement
Reaction between nitrosobenzenes and HCl resulting in rearrangement.
Fries Rearrangement
Rearrangement of phenolic esters with Lewis acid catalyst.
Gatterman Reaction
Reaction between aryls and zinc nitriles in HCl resulting in formylation.
Note: Variation of the Vilsmeier-Haack formylation.
Henkel Reaction
Rearrangement of phthalates to terphthalates with cadmium catalyst.
Hofmann-Martius Rearrangement
Reaction between secondary amines and HCl resulting in rearrangement of the R group.
Houben-Hoesch Reaction
Reaction between aryls and nitriles in HCl resulting in acylation.
Note: Variation of Friedel-Crafts acylation.
Jacobsen Rearrangement
Reaction between polyalkylbenzenes and H2SO4 resulting in sulfonation and rearrangement of alkyl groups.
Note: Usually, the polyalkylbenzene must have four or more alkyl groups.
Orton Rearrangement
Reaction between an N-chloro arylamines and HCl causes migration of the chloride.
Vilsmeier-Haack Reaction
Also known as: Vilsmeier-Haack formylation
Reaction between aryls, disubstituted formamides and POCl3 resulting in formylation.