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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.

M2782_01

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