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

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. (C) 2013 Elsevier B.V. All rights reserved.