N‐Directed defluorinative γ‐C(sp3)−H allylation of sulfamate esters for synthesis of gem‐difluoroalkenes via photoredox catalysis

Author:

Yang Jia‐Wen1,Li Meng1,Tan Guang‐Qiang1,Liu Feng12,Qin Hai‐Tao1ORCID

Affiliation:

1. Jiangsu Key Laboratory of Neuropsychiatric Diseases and Department of Medicinal Chemistry College of Pharmaceutical Sciences, Soochow University 199 Ren-Ai Road, Suzhou Jiangsu 215123 People's Republic of China

2. Jiangsu Province Engineering Research Center of Precision Diagnostics and Therapeutics Development College of Pharmaceutical Sciences, Soochow University 199 Ren-Ai Road, Suzhou Jiangsu 215123 People's Republic of China

Abstract

Abstractgem‐Difluoroalkenes are unique structural motifs with important applications ranging from drugs to materials. Herein, we report a novel radical‐mediated defluorinative allylation of sulfamate esters with through distal C(sp3)−H functionalization under photoredox conditions. The reaction could readily incorporate various gem‐difluoroalkene motifs into previously unfunctionalized sp3 carbon centers. The transformation allows directly dual activation of N−H and C(sp3)−H bonds via a photocatalytic and redox‐neutral process, as well as using water as environmentally friendly co‐solvent. The reaction could provide a general and operationally simple method to access gem‐difluoroalkene compounds with high diversity.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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