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Updated: Jul 27, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Preparation and Reactivity Study of a Versatile Trifluoromethylthiolating Agent: S-Trifluoromethyl
Yuhao Yang1, Seyedesahar Miraghaee1, Renee Pace1
1Department of Chemistry, University of Louisville, Louisville, KY 40292, USA.
Abstract:
A novel, air and thermally stable, yet highly reactive trifluoromethylthiolating reagent, CF3 SO2 SCF3 (1), was prepared easily in one step from commercially inexpensive CF3 SO2 Na and Tf2 O. 1 is a highly versatile and atom-efficient reagent that can generate one equivalent of CF3 S+ , two equivalents of CF3 S- , or a combination of CF3 S⋅/CF3 ⋅ species. Many high-yielding CF3 S reactions of C, O, S, and N-nucleophiles were achieved, including the simple-step preparations of many reported CF3 S reagents. 1 delivered a hitherto hard-to-synthesize ArOSCF3 that was followed by a novel CF3 SII -rearrangement. Through Cu or TDAE/Ph3 P combinations, 1 generated two equivalents of CF3 S anion species, and the photo-catalyzed reactions of alkenes with 1 provided CF3 /CF3 S-containing products in high atom-efficiency.
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