Fukuyama reduction

Fukuyama reduction
Named after Tohru Fukuyama
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal 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.[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.

Reaction mechanism

The basic reaction mechanism for this reaction takes place as a catalytic cycle:

Scope

In a variation of the Fukuyama reduction the core BODIPY molecule has been synthesized from the SMe-substituted derivative:[2][3]

In the related Fukuyama coupling the hydride is replaced by a carbon nucleophile.

References

  1. ↑ 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 doi:10.1021/ja00175a043
  2. ↑ The Smallest and One of the Brightest. Efficient Preparation and Optical Description of the Parent Borondipyrromethene System. I. J. Arroyo, R. Hu, G. Merino, B. Z. Tang, E. Peña-Cabrera, J. Org. Chem. 2009, ASAP
  3. ↑ Additional reagents CuTC, Pd(dba)2, tri(2-furyl)phosphine
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