Sulfonamide for Nucleophilic and Electrophilic Trifluoromethylthiolations

N-Methyl-N-[(trifluoromethyl)thio]-p-toluenesulfonamide (1) has good utility in the trifluoromethylthiolation of a variety of substrates and functional groups. 1 reacts in an electrophilic manner when reacting with enolates¹⁾, whereas benzyl halides or benzyl alcohol derivatives react nucleophically³⁾ to afford trifluoromethylthiolated products. Furthermore, in the presence of catalytic amount of copper iodide(I), 1 reacts with boronic acids to provide trifluoromethylthiolated products via Suzuki-Miyaura type cross coupling reactions.²⁾ Thus, 1 is expected to be utilized as a trifluoromethylthiolating agent over a variety of reactions within the fields of medicinal chemistry, and in the development of functional materials.