Visible-Light-Induced Defluorinative α-C(sp3)-H Alkylation for the Synthesis of gem-Difluoroallylated α-Trifluoromethylamines

Bingran Chen; Qinlin Chen; Yang Liu; Jinxiu Chen; Xi Zhou; Haifeng Wang; Qiongjiao Yan; Wei Wang; Zeyu Cai; Fen-Er Chen

doi:10.1021/acs.orglett.3c03523

Visible-Light-Induced Defluorinative α-C(sp³)-H Alkylation for the Synthesis of gem-Difluoroallylated α-Trifluoromethylamines

Org Lett. 2023 Dec 29;25(51):9124-9129. doi: 10.1021/acs.orglett.3c03523. Epub 2023 Nov 17.

Authors

Bingran Chen¹, Qinlin Chen¹, Yang Liu¹, Jinxiu Chen¹, Xi Zhou¹, Haifeng Wang¹, Qiongjiao Yan¹, Wei Wang¹, Zeyu Cai², Fen-Er Chen^{1

3

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Affiliations

¹ Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205, P. R. China.
² Hubei Duorui Pharmaceutical Co., Ltd. Wuhan 430205, P. R. China.
³ Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, P. R. China.
⁴ Shanghai Engineering Center of Industrial Catalysis for Chiral Drugs, Shanghai 200433, P. R. China.

PMID: 37976410
DOI: 10.1021/acs.orglett.3c03523

Abstract

Herein, we describe a novel and efficient photoredox catalytic C_α radical addition/defluoroalkylation coupling reaction between α-trifluoromethyl alkenes and N-trifluoroethyl hydroxylamine. A series of gem-difluoroallylated α-trifluoromethylamines were synthesized by the C_α radical addition enabled by a 1,2-H shift of the in situ-generated N-trifluoroethyl radical. Notably, this protocol is distinguished by its mild conditions, easy operation, and excellent functional group tolerability.