Efficient synthesis of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts for electrophilic bromodifluoromethylating reagents

Abstract

A series of unsymmetrical S-(bromodifluoromethyl)diarylsulfonium salts 1 were readily synthesized by treatment of corresponding (bromodifluoromethyl)arylsulfoxides 2 and substituted benzenes 3 with triflic anhydride in moderate to good yields. The unsymmetrical sulfonium salts 1 with different aryl groups having electron-donating or electron-withdrawing substituents can be nicely constructed depending on the choice of 2 and 3. Bromodifluoromethylation of alkynes was evaluated by using the selected diarylsulfonium salts 1 to provide the desired bromodifluoromethylated alkynes in moderate to good yields.