TY - CHAP
T1 - Aldehydes
T2 - qryl and heteroaryl aldehydes
AU - Aldabbagh, F.
PY - 2005
Y1 - 2005
N2 - A comprehensive review of aromatic aldehyde preparations, published since 1995, is described. New methods include the introduction of new reducing reagents that convert benzoic acids and benzoyl halides into aldehydes. Alternatives to the use of DIBAL-H for the reduction of aromatic esters, amides, and nitriles into aldehydes are described. The Sommelet reaction, oxidations of benzyl halides, benzylamines, toluenes, oxidative cleavages of aryl ethylenes, and numerous selective oxidations of benzylic alcohols to aldehydes are reviewed. DDQ has been used to selectively oxidize benzyl ethers and carbamates. Pd-catalyzed formylation of aryl halides, and organolithum and Grignard-hydrogen or halogen exchanges followed by quenching of the carbanion with a formylating reagent are described. Electrophilic formylations of arenes include the Duff, Reimer"Tiemann, Vilsmeier"Haack, Gattermann"Koch, and Gattermann reactions. Formylations using dichloromethyl methyl ether, and polyformamides under typical Friedel"Crafts conditions have been shown to be applicable to activated as well as nonactivated arenes. Selective ortho- and para-formylation of phenols and nitrobenzenes respectively is described. Preparations of dicarbaldehydes, polyaromatic, furan, benzofuran, thiophene, benzothiophene, pyrrole, indole, pyridine, quinoline, pyrazole, imidazole, benzimidazole, thiazole and miscellaneous aromatic and heterocyclic carboxaldehydes are included.
AB - A comprehensive review of aromatic aldehyde preparations, published since 1995, is described. New methods include the introduction of new reducing reagents that convert benzoic acids and benzoyl halides into aldehydes. Alternatives to the use of DIBAL-H for the reduction of aromatic esters, amides, and nitriles into aldehydes are described. The Sommelet reaction, oxidations of benzyl halides, benzylamines, toluenes, oxidative cleavages of aryl ethylenes, and numerous selective oxidations of benzylic alcohols to aldehydes are reviewed. DDQ has been used to selectively oxidize benzyl ethers and carbamates. Pd-catalyzed formylation of aryl halides, and organolithum and Grignard-hydrogen or halogen exchanges followed by quenching of the carbanion with a formylating reagent are described. Electrophilic formylations of arenes include the Duff, Reimer"Tiemann, Vilsmeier"Haack, Gattermann"Koch, and Gattermann reactions. Formylations using dichloromethyl methyl ether, and polyformamides under typical Friedel"Crafts conditions have been shown to be applicable to activated as well as nonactivated arenes. Selective ortho- and para-formylation of phenols and nitrobenzenes respectively is described. Preparations of dicarbaldehydes, polyaromatic, furan, benzofuran, thiophene, benzothiophene, pyrrole, indole, pyridine, quinoline, pyrazole, imidazole, benzimidazole, thiazole and miscellaneous aromatic and heterocyclic carboxaldehydes are included.
U2 - 10.1016/B0-08-044655-8/00048-9
DO - 10.1016/B0-08-044655-8/00048-9
M3 - Entry for encyclopedia/dictionary
SN - 9780080446554
VL - 3
T3 - Chemistry, Molecular Sciences and Chemical Engineering
SP - 99
EP - 133
BT - Comprehensive Organic Functional Group Transformations II
A2 - Katritzky , Alan R.
A2 - Taylor, Richard J.K.
PB - Elsevier Ltd
CY - Oxford U.K.
ER -