1-[hydroxy(sulfonyloxy)iodo]-1H,1H-perfluoroalkanes: Stable, fluoroalkyl analogs of Koser's reagent

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

Research output: Contribution to journalArticle

24 Scopus citations

Abstract

1-[Hydroxy(sulfonyloxy)iodo]-1H,1H/-perfluoroalkanes 3 [RfCH2I(OH)OSO2R; R = CH3, CH3, p-CH3C6H4, Rf = CF3, C2F5] can be prepared in two steps from the appropriate iodofluoroalkanes by oxidation with peroxytrifluoroacetic acid and subsequent reaction with TsOH, MsOH, or Me3SiOTf. The tosylate derivative 3a reacts with silyl enol ethers under mild conditions to give the respective α-(tosyloxy) ketones. A similar reaction of cyclohexene furnishes cis-1,2-bis(tosyloxy)cyclohexane as the major product. Triflates 3c,f react with (trimethylsilyl)arenes under mild conditions to afford the respective (fluoroalkyl) (aryl)iodonium triflates 7, while the analogous reaction with alkynyltrimethylsilanes leads to novel (fluoroalkyl)(alkynyl)iodonium salts 8.

Original languageEnglish (US)
Pages (from-to)8272-8276
Number of pages5
JournalJournal of Organic Chemistry
Volume61
Issue number23
StatePublished - Nov 15 1996

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