Journal
ORGANIC LETTERS
Volume 24, Issue 35, Pages 6380-6385Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02294
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Funding
- Research Grants Council of Hong Kong [CUHK 14304421]
- Chinese University of Hong Kong (Faculty of Science-Direct Grant for Research)
- Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
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In this paper, we describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-beta-monofluoroacrylates, which yields trisubstituted (Z)-alkene products with excellent diastereoselectivity and an inversion of double bond geometry. Experimental and computational studies demonstrate that Rh(I)-facilitated beta-F elimination is preferred over competing beta-H elimination and protodemetalation.
We herein describe a highly selective Rh(I)-catalyzed defluorinative coupling of boronic acids with (E)-beta-monofluoroacrylates. In contrast to previous methods, the trisubstituted (Z)-alkene products were obtained in excellent dr with an inversion of double bond geometry. Experimental and computational studies established that Rh(I)-facilitated beta-F elimination is favored over competing beta-H elimination and protodemetalation.
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