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.
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.
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.