中国化学快报(英文版)2024,Vol.35Issue(9) :155-159.DOI:10.1016/j.cclet.2024.109502

Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines

Boqiang Wang Yongzhuo Xu Jiajia Wang Muyang Yang Guo-Jun Deng Wen Shao
中国化学快报(英文版)2024,Vol.35Issue(9) :155-159.DOI:10.1016/j.cclet.2024.109502

Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines

Boqiang Wang 1Yongzhuo Xu 1Jiajia Wang 1Muyang Yang 1Guo-Jun Deng 2Wen Shao1
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作者信息

  • 1. Key Laboratory for Green Organic Synthesis and Application of Hunan Province,Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education,College of Chemistry,Xiangtan University,Xiangtan 411105,China
  • 2. Key Laboratory for Green Organic Synthesis and Application of Hunan Province,Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education,College of Chemistry,Xiangtan University,Xiangtan 411105,China;Department School of Chemistry and Chemical Engineering,Henan Normal University,Xinxiang 453007,China
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Abstract

A highly site-selective intermolecular trifluoromethylimination of activated and unactivated olefins was reported under transition-metal-and photosensitizer-free conditions.This newly developed strategy pro-vides straightforward and efficient access to diverse value-added vicinal trifluoromethyl amines without resorting to the pre-functionalized reagents.Mechanistic experiments demonstrate that the approach pro-ceeded through CF3 and iminyl two-radicals process,which were generated directly from commercially available benzophenone imine in a novel electron-donor mode via a SET process activated by the bifunc-tional hypervalent iodine reagents.The synthetic potential of the protocols was further showcased via the condensation/amination sequential cascade,and transformations to access β-CF3 primary amines.

Key words

Transition-metal free/Alkenes difunctionalization/Amination/Trifluoromethylation/Single-electron transfer

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出版年

2024
中国化学快报(英文版)
中国化学会

中国化学快报(英文版)

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影响因子:0.771
ISSN:1001-8417
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