Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide

• Sébastien Alazet,
• Kevin Ollivier and
• Thierry Billard

Beilstein J. Org. Chem. 2013, 9, 2354–2357, doi:10.3762/bjoc.9.270

• 10.3762/bjoc.9.270 Abstract The CF3SN moiety is a substituent with interesting properties. However, there is no easy synthetic access to molecules bearing this group. The trifluoromethanesulfenamide is a new reagent for the electrophilic trifluoromethylthiolation which reacts easily with amines to obtain

• trifluoromethylsulfanylamines with good yields. Keywords: amine; fluorine; organo-fluorine; trifluoromethanesulfenamide; trifluoromethylsulfanylamine; trifluoromethylthiolation; Introduction In past decades, fluorinated molecules have found more and more applications in a variety of fields, especially in the design of new

• panel of trifluoromethylsulfanylamines. The trifluoromethanesulfenamide 1a is an efficient reagent for the electrophilic trifluoromethylthiolation of carbon nucleophiles [38][39][40][41][42][43][44]. Therefore, this reagent should react with amines to perform transamination reactions with secondary