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Photochemical Alkene Trifluoromethylimination Enabled by Trifluoromethylsulfonylamide as a Bifunctional Reagent

Yu Zheng, Zihao Liao, Zhenzhen Xie, Hongbin Chen, Kai Chen, Haoyue Xiang* and Hua Yang*

*College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China, Email: xianghaoyuecsu.edu.cn, hyangchemcsu.edu.cn

Y. Zheng, Z. Liao, Z. Xie, H. Chen, K. Chen, H. Xiang, H. Yang, Org. Lett., 2023, 25, 2129-2133.

DOI: 10.1021/acs.orglett.3c00577


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Abstract

N-(Diphenylmethylene)-1,1,1-trifluoromethanesulfonamide is a bench-stable and readily accessible carboamination reagent, that enables a facile and versatile trifluoromethylimination of alkenes under metal-free photocatalytic conditions. The mild reaction conditions and good functional group compatibility render this protocol highly valuable for the difunctionalization of olefins.


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proposed mechanism



Key Words

protected primary amines, benzylic amines, trifluoromethylation, photochemistry


ID: J54-Y2023