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Synfacts 2021; 17(05): 0541
DOI: 10.1055/s-0040-1719710
Metals in Synthesis

The Fukuyama Cross-Coupling Reaction

Contributor(s):
Mark Lautens
,
Randy Sanichar
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.
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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.


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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.


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Review

J. Lou, Q. Wang, P. Wu, H. Wang, Y.-G. Zhou, Z. Yu Chem. Soc. Rev. 2020, 49, 4307–4359.


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Publication History

Article published online:
20 April 2021

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