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

doi:10.1016/0040-4039(95)00275-H

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

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	2203-2206
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	13
DOIs	https://doi.org/10.1016/0040-4039(95)00275-H
State	Published - Mar 27 1995

Bibliographical note

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

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

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.",

author = "Viktor Zhdankin and Kuehl, {Chris J.} and Simonsen, {Angela J.}",

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T2 - Stable, fluoroalkyl analogs of Koser's reagent

AU - Zhdankin, Viktor

AU - Kuehl, Chris J.

AU - Simonsen, Angela J.

N1 - Funding Information: This work was supported by an award from Research Corporation.

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AB - 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.

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