Fukuyama reduction
Introduction 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. In the original scope of the reaction the silyl hydride was triethylsilane and the catalyst palladium on carbon::The Fukuyama reductionFukuyama 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
Scope In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative: Additional reagents are copper(I)-thiophene-2-carboxylate (CuTC), Pd(dba)2 and tri(2-furyl)phosphine:BODIPY synthesis Arroyo 2009In the related Fukuyama coupling the hydride is replaced by a carbon nucleophile.
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