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Fukuyama Coupling

The palladium-catalyzed coupling of organozinc compounds with thioesters to form ketones. This reaction tolerates a variety of functional groups due to the low reactivity of the organozinc reagents.

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Mechanism of the Fukuyama Coupling

Oxidative addition of the thioester is followed by transmetalation from the zinc compound. Reductive elimination leads to the coupled product.

Recent Literature

Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP
S.-Q. Tang, J. Bricard, M. Schmitt, F. Bihel, Org. Lett., 2019, 21, 844-848.

Facile Palladium-Mediated Conversion of Ethanethiol Esters to Aldehydes and Ketones
H. Tokuyama, S. Yokoshima, T. Yamashita, S.-C. Lin, L. Li, T. Fukuyama, J. Braz. Chem. Soc., 1998, 9, 381-387.