1-[Hydroxy(sulfonyloxy)iodo]-2,2,2-trifluoroethanes, CF3CH2I(OH)OSO2R: Stable, fluoroalkyl analogs of Koser's reagent

Article abstract of DOI:10.1016/0040-4039(95)00275-H

1-[Hydroxy(sulfonyloxy)iodo]-2,2,2-trifluoroethanes [CF₃CH₂I(OH)OSO₂R; R = CH₃, CF₃, p-CH₃C₆H₄] can be prepared in two steps from trifluoroethyliodide by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH, MsOH, or Me₃SiOTf. Reaction of the tosylate derivative 3 with silyl enol ethers affords α-tosyloxyketones, while triflate 5 smoothly reacts with trimethylsilylbenzene to give the respective trifluoroethyl(phenyl)iodonium triflate 8.