Palladium-Catalyzed Cross-Coupling of Cyanohydrins with Aryl Bromides: Construction of Biaryl Ketones

Jadab Majhi, Bohang Zhou, Yuxin Zhuang, Mai-Jan Tom, Huifang Dai*, P. Andrew Evans*

*Fudan University, 826 Zhangheng Rd, Shanghai 201203, China; Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada, Email: hfdaifudan.edu.cn, Andrew.Evanschem.queensu.ca

J. Majhi, B. Zhou, Y. Zhung, M.-J. Tom, H. Dai, P. A. Evans, Synthesis, 2023, 55, 1752-1763.

DOI: 10.1055/a-1850-3687

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Abstract

A palladium-catalyzed cross-coupling of the lithium anion of aryl tert-butyldimethylsilyl-protected cyanohydrins with aryl bromides followed by in situ deprotection with fluoride ion provides a convenient and versatile approach to biaryl ketones. This protocol represents an example of a palladium-catalyzed arylation of a cyanohydrin, which functions as an acyl anion equivalent.

see article for more examples

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Key Words

acyl anions, aryl halides, aryl ketones, cyanohydrins, palladium catalysis

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ID: J66-Y2023