Stereoselective Defluorinative Thiolation of gem-Difluoroalkenes with Thiols via Nucleophilic Substitution
Xin Guo1, Dandan Xia1, Huanyi Guo1
1Guizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy, Zunyi Medical University, Zunyi563003, P.R. China.
Abstract:
Monofluoroalkenes are valuable mimics of enol and amide bonds, making them important structural motifs in drug discovery. Herein, we report a transition-metal-free, stereoselective defluorinative thiolation of gem-difluoroalkenes with thiols under simple base promotion. This transformation proceeds efficiently through a nucleophilic substitution pathway, affording a broad array of monofluoroalkenyl sulfides in generally good yields with excellent stereoselectivities (Z/E up to 24:1). This protocol features a broad substrate scope and excellent functional group tolerance, representing a convenient approach to stereodefined monofluoroalkenyl sulfides.
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