Selective and Scalable Synthesis of Trifluoromethanesulfenamides and Fluorinated Unsymmetrical Disulfides using a Shelf-Stable Electrophilic SCF3Reagent.
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.
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen (Germany).
Roman
R
Pluta
Magnus
M
Rueping
SN bond formation; fluorine; sulfenamides; synthetic methods; trifluoromethanesulfenylation