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 [1]. Advantages are high chemoselectivity, mild reaction conditions and the use of less-toxic reagents [2].

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 [3]

This reaction was preceded by the conceptually related Fukuyama reduction.

References

  1. ^ 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
  2. ^ Org. Synth. 2007, 84, 285-294 http://orgsynth.org/orgsyn/pdfs/V84P0285.pdf
  3. ^ 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