Syntheses and properties of (perfluoroalkyl)phenyliodonium triflates (fits reagents) and their analogues

Article abstract of DOI:10.1016/S0022-1139(00)85087-3

A variety of (per- and polyfluoroalkyl)phenyl- and p-fluorophenyliodonium triflates 3 were synthesized in good yields by the oxidation of the corresponding iodofluoroalkanes with trifluoroperacetic acid followed by the treatment with benzene or fluorobenzene and triflic acid. It was also shown that elemental fluorine was used as a substitute for the peracid. The use of fluorosulfonic, sulfuric, and methanesulfonic acids instead of triflic acid afforded the fluoroalkylaryliodonium fluorosulfonates 5, sulfates 6, and methanesulfonate 7, respectively. Similarly perfluoroalkylene-α,ω-bisaryliodonium triflates 10 were synthesized from α,ω-diiodoperfluoroalkanes. On the other hand, the treatment of (perfluoroalkyl)-p-tolyliodonium chlorides with silver sulfonates gave the iodonium benzenesulfonate 13, methanesulfonate 12, and triflate 14, and bisiodonium sulfate 15. Thermolysis of (perfluorooctyl)phenyliodonium triflate at about 150°C afforded perfluorooctyl triflate, iodobenzene, and (perfluorooctyl)iodobenzene in 73, 63, and 25% yields, respectively.