Fukuyama reduction | |
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Named after | Tohru Fukuyama |
Reaction type | Organic redox reaction |
Identifiers | |
Organic Chemistry Portal | fukuyama-reduction |
RSC ontology ID | RXNO:0000680 |
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. [1] In the original scope of the reaction the silyl hydride was triethylsilane and the catalyst palladium on carbon:
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.
The basic reaction mechanism for this reaction takes place as a catalytic cycle:
In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative: [2] Additional reagents are copper(I)-thiophene-2-carboxylate (CuTC), Pd(dba)2 and tri(2-furyl)phosphine
In the related Fukuyama coupling the hydride is replaced by a carbon nucleophile.