Fukuyama coupling

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 ["A novel ketone synthesis by a palladium-catalyzed reaction of thiol esters and organozinc reagents" Tetrahedron Letters, Volume 39, Issue 20, 14 May 1998, Pages 3189-3192 Hidetoshi Tokuyama, Satoshi Yokoshima, Tohru Yamashita and Tohru Fukuyama doi|10.1016/S0040-4039(98)00456-0] . Advantages are high chemoselectivity, mild reaction conditions and the use of less-toxic reagents [Org. Synth. 2007, 84, 285-294 http://orgsynth.org/orgsyn/pdfs/V84P0285.pdf] .

:

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.

:

The reaction (interrupted) has been used in the synthesis of biotin ["Facile synthesis of (+)-biotin via Fukuyama coupling reaction" Toshiaki Shimizu and Masahiko S Tetrahedron Letters Volume 41, Issue 26, 24 June 2000, Pages 5099-5101 doi|10.1016/S0040-4039(98)00456-0]

:

References