Rhodium-catalyzed formal [4+3] annulation reaction of N-methoxybenzamides with gem-difluorocyclopropenes: A combination of experimental and theoretical studies

A rhodium-catalyzed [4+3] cycloaddition reaction between N-methoxybenzamides and gem-difluorocyclopropenes is described. The reaction offers a mild and efficient approach towards the synthesis of fluorinated 2H-azepin-2-ones with broad substrate scope. A consecutive HOAc-assisted C-N bond formation and fluorine elimination are involved as key steps for success as illustrated by detailed DFT studies. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

Automated summary

This article describes a rhodium-catalyzed reaction for the synthesis of fluorinated 2H-azepin-2-ones. The reaction is mild and efficient, with a broad substrate scope. The key steps for success are consecutive C-N bond formation and fluorine elimination.