Silver‐Catalyzed Nucleophilic Deoxydifluoromethylthiolation of Activated Aliphatic Alcohols with BT−SCF2H

Abstract

AbstractDeoxygenative conversion of alcohols into difluoromethylthioethers is reported using 2‐((difluoromethyl)thio)‐3‐methylbenzo[d]thiazol‐3‐ium triflate (BT−SCF2H) as a source of −SCF2H anions. The presence of silver(I) triflate as a catalyst was found to be crucial for stabilizing the in situ‐generated anion, while the concomitant formation of a reactive 2‐(alkoxy)benzothiazolium electrophile likely ensures a fast onward substitution reaction, avoiding the build‐up of −SCF2H. To the best of our knowledge, this process represents the first report of a direct nucleophilic substitution reaction with −SCF2H and delivers products containing the medicinally relevant difluoromethylthio motif in a single step from widely available alcohols.