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. 2020 Dec 4;85(23):15676-15685.
doi: 10.1021/acs.joc.0c02157. Epub 2020 Oct 30.

Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides

Fusheng Bie  1   2 , Xuejing Liu  1   2 , Yijun Shi  1   2 , Han Cao  1   2 , Ying Han  1   2 , Michal Szostak  3 , Chengwei Liu  3
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Rh-Catalyzed Base-Free Decarbonylative Borylation of Twisted Amides

Fusheng Bie et al. J Org Chem. .

Abstract

We report the rhodium-catalyzed base-free decarbonylative borylation of twisted amides. The synthesis of versatile arylboronate esters from aryl twisted amides is achieved via decarbonylative rhodium(I) catalysis and highly selective N-C(O) insertion. The method is notable for a very practical, additive-free Rh(I) catalyst system. The method shows broad functional group tolerance and excellent substrate scope, including site-selective decarbonylative borylation/Heck cross-coupling via divergent N-C/C-Br cleavage and late-stage pharmaceutical borylation.

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