Trifluoromethylthiolating Agent Usable for Direct Dehydroxytrifluoromethylthiolation of Alcohols

Silver(I) trifluoromethanethiolate (1) has already been known as a trifluoromethylthiolating agent^1,2) and is also applicable to direct dehydroxytrifluoromethylthiolation.³⁾ 1 successfully gives trifluoromethanethiolate (2) by treatment with tetrabutylammonium iodide (TBAI) or potassium iodide.⁴⁾ 2 is unstable and is known to decompose into carbonothioic difluoride (3) and fluoride anion. 3 reacts with alcohols to form an intermediate 4. Then, 4 reacts with 2 to afford the corresponding trifluoromethylthiolated product. The trifluoromethylthiolation by using 1 can be applied to alcohols with other functional groups and heterocyclic compounds, so that it is expected to be used in medicinal chemistry.