Visible-Light-Driven Iron-Catalyzed 1,2-Difluoroalkylthiolation of Alkenes
Leifeng Yuan1, Zemin Wang1, Wenli Zhuang1
1State Key Laboratory of Microbial Technology, Shandong University, 72 Binhai Road, Qingdao 266237, Shandong, P. R. China.
Abstract:
The synthesis of medicinally interesting aryldifluoromethylated compounds has drawn significant research attention in recent years. Herein, we report an unprecedented iron-mediated process for the selective defluorination of trifluoromethylarenes to achieve the 1,2-difluoroalkylthiolation of alkenes. Preliminary mechanistic studies revealed that thiolate anion, trifluoromethylarene, and iron cation could form an electron donor-acceptor (EDA) complex, which induced selective defluorination and then difunctionalization of alkenes to obtain aryldifluoromethylated products. The generated aryldifluoromethylated compounds make it difficult to form an EDA complex again, thus avoiding excessive defluorination. This conversion has concise and ambient reaction conditions and provides an alternative solution for obtaining difluorobenzylic intermediates.
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