First and second generation of trifluoromethanesulfenamide reagent: A trifluoromethylthiolating comparison

• Group SCF3 group is very lipophilic.
• Large interest for CF3S-molecules in various applications.
• Direct electrophilic trifluoromethylthiolation reactions required.
• First and 2nd generation of trifluoromethanesulfenamides are good reagents.
• Comparison of the reactivity of these reagents.

Trifluoromethylthiolation of molecules is a more and more studied reaction. In particular, the direct electrophilic trifluoromethylthiolation plays an important role in this chemistry. Among the various developed reagents, trifluoromethanesulfenamides constitute an efficient family of reagents. However, no systematic comparison of these two generations has been realized. In this paper, the difference of reactivity of these reagents is studied towards various nucleophiles.

The 1st and 2nd generation of trifluoromethanesulfenamides are efficient reagents for direct electrophilic trifluoromethylthiolations. Both reagents are complementary and the optimal selection is depending on the targeted compounds.Figure optionsDownload as PowerPoint slide