Fukuyama coupling

Overview
The Fukuyama coupling is a coupling reaction taking place between a thioester and an organozinc halide in the presence of a palladium catalyst. The reaction product is a ketone. This reaction was discovered by Tohru Fukuyama et al. in 1998. Advantages are high chemoselectivity, mild reaction conditions and the use of less-toxic reagents.


 * [[Image:FukuyamaCoupling.svg|Fukuyama coupling]]

One advantage of this method is that the reaction stops at the ketone and does not proceed to a tertiary alcohol. In addition, the protocol is compatible with functional groups such as ketones, acetates, sulfides, aromatic bromides, chlorides and aldehydes.


 * [[Image:Fukuyama1998.svg|600px|Original Fukuyama 1998 reaction]]

The reaction (interrupted) has been used in the synthesis of biotin


 * [[Image:Biotin2000 synthesis.svg|600px|Biotin total synthesis]]