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

He, Yimiao*; Tian, Limei; Chang, Xuexue; Qu, Zeming; Huang, Yanmin; Huang, Chusheng; Sun, Qing*; Wang, Honggen*
Science Citation Index Expanded
南昌航空大学; 中山大学

摘要

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.

关键词

gem-Difluorocyclopropene Fluorinated 2H-azepin-2-one C-H functionalization Oxidizing directing group Rhodium [4+3] Annulation