Reductive insertion of sulfur dioxide for the synthesis of trifluoromethyl thiolsulphonates through a one-pot reaction of aniline and trifluoromethanesulfanylamide

A bismuth(III) chloride-mediated one-pot reaction of anilines, sulfur dioxide, and trifluoromethanesulfanylamide is reported herein, leading to antifungal trifluoromethyl thiolsulphonates. This transformation employs N-aminomorphine as an additive and provides the final products in good yields with a broad functional group tolerance. It is believed that bismuth(III) chloride facilitates the formation of "CF3S+", and N-aminomorphine plays a critical role in providing electrons to catalyse the cross-coupling of in situ generated aryldiazonium, sulfur dioxide and trifluoromethanesulfanylamide.