Ion-radical perfluoroalkylation. Part 11. Perfluoroalkylation of thiols by perfluoroalkyl iodides in the absence of initiators

Selective fluoroalkylation of thiophenols by 1,2-dibromotetrafluoroethane activated by sulfur dioxide

“…(1) can be rationalized by an ionic chain mechanism postulated in [10][11][12][13][14][15][16][17][18], including anionic intermediates ArSCF 2 CF 2 À . Reaction with proton donors, including H 2 O, gives the side product, ArSCF 2 CF 2 H, lowering the yield of the desired ArSCF 2 CF 2 Br.…”

“…Introduction of halocarbon fragments, containing other halogen atoms besides fluorine, into different organic substrates allows the synthesis of new polyfluoroalkyl substrates as well as transformation of fluorine containing substituents to more complex groups [1][2][3][4][5][6][7][8][9][10][11][12][13][14].…”

Synthesis of trifluoromethylated heterocycles using partially fluorinated epoxides

“…The treatment of 9 by t-BuOK in DMF solvent followed by reaction with C 6 F 13 I at 50-80 8C results in perfluoroalkylation of intermediate 10a and selective formation of sulfide 11. The mechanism of perfluoroalkylation probably involves a single electron transfer step, a process which is well established for the reaction of thiols with R F I [28].…”

Chain-radical fluoroalkylation of thiophenols with freon ClCF2CFCl2 in the presence of sulfur dioxide

“…Alternatively, for bromo-and iodofluoroalkanes, in some cases it is possible to implement thiophenols fluoroalkylation by a chainradical route [8,14,15]. Such processes exhibit sufficiently high selectivity.…”