Development of (2-bromo-1,1,2,2-tetrafluoroethyl)(phenyl)sulfane as tetrafluoroethyl-radical and tetrafluoroethylene-diradical synthons for additions to alkenes

• PhSF2CF2Br undergoes radical addition to alkenes with tributyltin hydride and triethylborane.
• Phenylsufanyl group reduction of the formed adducts gives compounds with the tetrafluoroethyl group.
• Radical addition of the adducts to alkenes provides tetrafluoroethylene-containing products.

PhSCF2CF2Br in the presence of tributyltin hydride and substochiometric triethylborane in dichloromethane underwent radical addition to alkenes to give the bromine-free products. Reductive substitution of the phenylsulfanyl group for hydrogen in these adducts provided compounds with the tetrafluoroethyl group. Under the same conditions and in the presence of alkenes, radical addition took place to furnish tetrafluoroethylene-containing alkanes.

Figure optionsDownload as PowerPoint slide