Ammonium Chloride-Mediated Trifluoromethylthiolation of p‑Quinone Methides

Ammonium chloride-mediated trifluoromethylthiolation of p-quinone methides is reported using inexpensive and bench stable AgSCF₃ as a nucleophilic trifluoromethylthiolating (-SCF₃) reagent. This method is an efficient strategy for the construction of the benzylic C­(sp³)–SCF₃ bond to synthesize trifluoromethylthio-diarylmethane derivatives by 1,6-conjugate addition/aromatization under mild reaction conditions without any metal catalyst, oxidants, or additives. This is the first report of trifluoromethylthiolation of p-quinone methides. In addition, di-trifluoromethylthiolation of δ-chloro-p-quinone methide and scalability are demonstrated.