Synthesis of Fluoroalkyl Sulfides via Additive-Free Hydrothiolation and Sequential Functionalization Reactions

A modular synthetic method, involving a hydrothiolation, silylation, and fluoroalkylation, for the construction of highly functionalized fluoroalkyl sulfides has been developed. The use of aprotic polar solvents enables the additive-free chemoselective hydrothiolation of tetrafluoroethylene, trifluorochloroethylene, and hexafluoropropene with various thiols. The stepwise functionalization reactions convert the hydrothiolated intermediates into the tetrafluoroethyl sulfides in high efficiency. The method avoids the use of the environmental pollutant Halon-2402, which was employed as a building block in a reported synthetic route.

Automated summary

A modular synthetic method has been developed for the construction of highly functionalized fluoroalkyl sulfides, avoiding the use of environmental pollutants. The stepwise functionalization reactions convert the hydrothiolated intermediates into tetrafluoroethyl sulfides efficiently.