Preparation and Reactivity Study of a Versatile Trifluoromethylthiolating Agent: S-Trifluoromethyl Trifluoromethanesulfonothioate (TTST) |
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Authors: | Yuhao Yang Seyedesahar Miraghaee Renee Pace Dr Teruo Umemoto Prof Gerald B Hammond |
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Institution: | Department of Chemistry, University of Louisville, Louisville, KY 40292 USA |
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Abstract: | A novel, air and thermally stable, yet highly reactive trifluoromethylthiolating reagent, CF3SO2SCF3 ( 1 ), was prepared easily in one step from commercially inexpensive CF3SO2Na and Tf2O. 1 is a highly versatile and atom-efficient reagent that can generate one equivalent of CF3S + , two equivalents of CF3S−, or a combination of CF3S⋅/CF3⋅ species. Many high-yielding CF3S reactions of C, O, S, and N-nucleophiles were achieved, including the simple-step preparations of many reported CF3S reagents. 1 delivered a hitherto hard-to-synthesize ArOSCF3 that was followed by a novel CF3SII-rearrangement. Through Cu or TDAE/Ph3P combinations, 1 generated two equivalents of CF3S anion species, and the photo-catalyzed reactions of alkenes with 1 provided CF3/CF3S-containing products in high atom-efficiency. |
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Keywords: | Atom-Economy CF3S Reagents Photocatalysis Rearrangement Trifluoromethylthiolation |
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