Citation: Yimiao He, Limei Tian, Xuexue Chang, Zeming Qu, Yanmin Huang, Chusheng Huang, Qing Sun, Honggen Wang. Rhodium-catalyzed formal [4 + 3] annulation reaction of N-methoxybenzamides with gem-difluorocyclopropenes: A combination of experimental and theoretical studies[J]. Chinese Chemical Letters, ;2022, 33(6): 2987-2992. doi: 10.1016/j.cclet.2022.01.068 shu

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

Yimiao He ^{a, *,} ,
Limei Tian ^{a, 1} ,
Xuexue Chang ^{a, 1} ,
Zeming Qu ^a ,
Yanmin Huang ^a ,
Chusheng Huang ^a ,
Qing Sun ^{b, *,} ,
Honggen Wang ^{c, *,}

a.
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, College of Chemistry and Materials, Nanning Normal University, Nanning 530001, China
b.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
c.
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

heyimiao@gxtc.edu.cn

sunqing@nchu.edu.cn

wanghg3@mail.sysu.edu.cn

Received Date: 21 December 2021
Revised Date: 22 January 2022
Accepted Date: 24 January 2022
Available Online: 2 February 2022

Figures(11)

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 CN bond formation and fluorine elimination are involved as key steps for success as illustrated by detailed DFT studies.
- gem-Difluorocyclopropene,
- Fluorinated 2H-azepin-2-one,
- C-H functionalization,
- Oxidizing directing group,
- Rhodium,
- [4+3] Annulation
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