Fukuyama reduction
Source: Wikipedia, the free encyclopedia.
Chemical reaction
Fukuyama reduction | |
---|---|
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
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:
- Oxidative addition:
- Transmetallation:
- Reductive elimination:
Scope
In a variation of the Fukuyama reduction the core
Pd(dba)2 and tri(2-furyl)phosphine
In the related
carbon nucleophile
.
References
- ^ 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