Superacid-Catalyzed Trifluoromethylthiolation of Aromatic Amines

Abstract

Upon activation under superacid conditions, functionalized tailor-made N-SCF₃ sulfenamides served as reagents for the trifluoromethylthiolation of aromatic amines. This method has a broad substrate scope and can be used for the late-stage functionalization of complex molecules such as alkaloids or steroids. Mechanistic studies based on in situ low-temperature NMR spectroscopy revealed the involvement of dicationic superelectrophilic intermediates.

Keywords: acidity; amines; fluorine; reaction mechanisms; superacidic systems.