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

Viktor Zhdankin, Chris J. Kuehl, Angela J. Simonsen

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2203-2206
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number13
DOIs
StatePublished - Mar 27 1995

Bibliographical note

Funding Information:
This work was supported by an award from Research Corporation.

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