Abstract: A series of 2-(trifluoroacetamido) imidazo [1, 2-a]-pyridines was prepared and treated with phenyliodine (III) bis (trifluoroacetate)(PIFA) in the presence of a variety of thiols leading chemoselectively to the corresponding 3-sulfides. Exposure of these adducts to silica gel in MeOH/CH2Cl2 provides a convenient method for the cleavage of the trifluoroacetamide group. Key words: chemoselective sulfenylation, phenyliodine (III) bis ( ...