Transition‐Metal‐Free Allylic Defluorination Cross‐Electrophile Coupling Employing Rongalite

Author:

Chen Xiang‐Long1,Wu Chun‐Yan1,Yang Dong‐Sheng1,Tang Bo‐Cheng2,Wang Huai‐Yu1,Yu Zhi‐Cheng1,Li Anling3,Wu Yan‐Dong1,Wu An‐Xin1

Affiliation:

1. National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry Central China Normal University Wuhan Hubei 430079 China

2. State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology The Hong Kong Polytechnic University Kowloon Hong Kong SAR China

3. Department of Clinical Laboratory, Center for Gene Diagnosis, and Program of Clinical Laboratory Medicine Zhongnan Hospital of Wuhan University Wuhan Hubei 430062 China

Abstract

Comprehensive SummaryThe conversion of CF3‐alkenes to gem‐difluoroalkenes using reductive cross‐coupling strategy has received much attention in recent years, however, the use of green and readily available reducing salt to mediate these reactions remains to be explored. In this work, a concise construction of gem‐difluoroalkenes, which requires neither a catalyst nor a metal reducing agent, was established. Rongalite, a safe and inexpensive industrial product, was employed as both a radical initiator and reductant. This procedure was compatible with both linear and cyclic diaryliodonium salts, enabling a wide variety of substrates (>70 examples). The utility of this approach was demonstrated through gram‐scale synthesis and efficient late‐stage functionalizations of anti‐inflammatory drugs.

Funder

National Natural Science Foundation of China

Publisher

Wiley

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