Remote trifluoromethylthiolation of alcohols under visible light

Article abstract of DOI:10.1016/j.tet.2020.131153

An unprecedented remote and regioselective trifluoromethylthiolation reaction of alcohols was developed. Under mild conditions, a panel of free-alcohols was selectively functionalized with TolSO₂SCF₃ reagent as the SCF₃ source in the presence of hypervalent iodide (PIDA) under blue light irradiation. This approach offered an operationally simple tool for the construction of a challenging C(sp³)-SCF₃ bond at the δ-position of an alcohol by C(sp³)-H bond functionalization. Initial mechanistic studies suggested a radical pathway.