Selective and Scalable Synthesis of Trifluoromethanesulfenamides and Fluorinated Unsymmetrical Disulfides using a Shelf-Stable Electrophilic SCF3 Reagent

The chemoselective trifluoromethylthiolation of nitrogen nucleophiles and thiols using N-(trifluoromethylthio) phthalimide under mild, metal-free conditions is described. A series of trifluoromethanesulfenamides and unsymmetrical disulfides is prepared from the corresponding aliphatic and aromatic amines and thiols in good yields. The reactions are operationally simple and tolerate a wide variety of functional groups. Trifluoromethanesulfenamides and disulfides belong to interesting classes of organic molecules which possess remarkable properties for medicinal and agrochemical applications.