Transition-metal-free trifluoromethylthiolation and difluoromethylthiolation of thiols with trifluoromethanesulfonyl chloride and difluoromethanesulfonyl chloride |
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| Authors: | Xia Zhao Tianjiao Li Bo Yang Di Qiu Kui Lu |
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| Institution: | 1. College of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry, Ministry of Education, Tianjin Normal University, Tianjin 300387, China;2. College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, China |
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| Abstract: | Triphenylphosphine-mediated metal-free trifluoromethylthiolation and difluoromethylthiolation of thiols by CF3SO2Cl and CHF2SO2Cl to synthesize trifluoromethyl disulfides and difluoromethyl disulfides, respectively, was achieved at room temperature. Iodine generated in situ from iodide facilitated this reaction via the formation of iodotriphenylphosphonium iodide which could serve as a reducing agent in this transformation. Readily available reagents and mild reaction conditions without transition-metals allow this protocol to be more practical than traditional methods. |
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| Keywords: | Thrifluoromethylthiolation Difluoromethylthiolation Thiol Trifluoromethanesulfonyl chloride Difluoromethanesulfonyl chloride |
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