Nickel-Catalyzed Stereospecific C-H Coupling of Benzamides with Epoxides

Angewandte Chemie
Shibo XuMasahiro Miura

Abstract

A Ni(OAc)2 -catalyzed C-H coupling of 8-aminoquinoline-derived benzamides with epoxides has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to form the corresponding 3,4-dihydroisocoumarins directly. Additionally, the nickel catalysis is stereospecific, and the cis- and trans-epoxides are converted into the corresponding cis- and trans-dihydroisocoumarins with retention of configuration, which is complementary to previously reported palladium catalysis. Moreover, while still preliminary, the Csp3 -H functionalization is also achieved in the presence of modified NiCl2 catalysts.

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Citations

Sep 28, 2018·Organic & Biomolecular Chemistry·Hongqing YaoChuan Wang
Feb 14, 2019·Organic & Biomolecular Chemistry·Fangpeng HuGuosheng Huang
Feb 28, 2019·Chemistry : a European Journal·Shibo XuMasahiro Miura
Sep 19, 2019·Chemistry, an Asian Journal·Tariq A ShahTharmalingam Punniyamurthy
Feb 10, 2021·Chemistry : a European Journal·Liam S Fitzgerald, Miriam L O'Duill
Jul 1, 2021·Chemical Society Reviews·Binlin ZhaoZhuangzhi Shi

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