|
The Fukuyama reduction is an organic reaction and an organic reduction in which a thioester is reduced to an aldehyde by a silyl hydride in presence of a catalytic amount of palladium. This reaction was invented in 1990 by Tohru Fukuyama.〔''Facile reduction of ethyl thiol esters to aldehydes: application to a total synthesis of (+)-neothramycin A methyl ether'' Tohru Fukuyama, Shao Cheng Lin, Leping Li J. Am. Chem. Soc., 1990, 112 (19), pp 7050–7051 〕 In the original scope of the reaction the silyl hydride was triethylsilyl hydride and the catalyst palladium on carbon: :The Fukuyama reduction Fukuyama reductions are used for the conversion of carboxylic acids (as thioester precursor) to aldehydes which is considered a difficult procedure because of the ease of secondary reduction to an alcohol. ==Reaction mechanism== The basic reaction mechanism for this reaction takes place as a catalytic cycle: * Oxidative addition: :R-C(O)-SR + Pd(0) → RC(O)-Pd(II)-SR * Transmetallation: :RC(O)-Pd(II)-SR + R3SiH → RC(O)-Pd(II)-H + R3Si-SR * Reductive elimination: : RC(O)-Pd(II)-H → RC(O)-H + Pd(0) 抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)』 ■ウィキペディアで「Fukuyama reduction」の詳細全文を読む スポンサード リンク
|