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Fukuyama reduction : ウィキペディア英語版
Fukuyama reduction
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)
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