Tokuyama H,
Yokoshima S,
Yamashita T,
Fukuyama T.
*
The University of Tokyo, Japan
A Novel Ketone Synthesis by a Palladium-Catalyzed Reaction of Thiol Esters and Organozinc
Reagents.
Tetrahedron Lett. 1998;
39: 3189-3192
DOI:
10.1016/S0040-4039(98)00456-0
Key words
palladium catalysis - Fukuyama cross-coupling - thioesters - alkylzinc
Significance
Fukuyama and co-workers reported a palladium-catalyzed cross-coupling between thioesters
and organozinc reagents to afford the corresponding ketone products. The reaction
proceeds under mild conditions, shows good functional group tolerance, and affords
access to the product in excellent yields.
Comment
The reaction tolerates the presence of sensitive functional groups within the thioester,
including aldehydes, ketones, acetates, and even aryl bromides/chlorides. The selectivity
supports a faster rate of oxidation into the C–S bond, versus oxidative addition into
the aryl halides, or nucleophilic addition to aldehydes.
Review
J. Lou, Q. Wang, P. Wu, H. Wang, Y.-G. Zhou, Z. Yu Chem. Soc. Rev. 2020, 49, 4307–4359.
