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Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes

Yuwei Zong, Yihan Tang and Gavin Chit Tsui*

*Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong SAR, China, Email: gctsuicuhk.edu.hk

Y. Zong, Y. Tang, G. C. Tsui, Org. Lett., 2022, 24, 6380-6385.

DOI: 10.1021/acs.orglett.2c02294


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Abstract

A highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-β-monofluoroacrylates provides trisubstituted (Z)-alkene products in excellent dr with an inversion of double bond geometry. Experimental and computational studies established that Rh(I)-facilitated β-F elimination is favored over competing β-H elimination and protodemetalation.

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Key Words

arylation


ID: J54-Y2022