[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes - new hypervalent iodine species and promising reagents for organic synthesis

Viktor Zhdankin; Chris Kuehl

doi:10.1016/S0040-4039(00)73166-2

[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes - new hypervalent iodine species and promising reagents for organic synthesis

Viktor Zhdankin, Chris Kuehl

Chemistry & Biochemistry

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18 Scopus citations

Abstract

[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (C_nF_2n+1I⁺OH{multiset union}^-OSO₂R, n = 3, 4, 6; R = p-CH₃C₆H₄, CF₃) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH or Me₃SiOTf. These compounds react with trimethylsilyl derivatives of aromatic compounds under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

Original language	English (US)
Pages (from-to)	1809-1812
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	12
DOIs	https://doi.org/10.1016/S0040-4039(00)73166-2
State	Published - Mar 21 1994

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title = "[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes - new hypervalent iodine species and promising reagents for organic synthesis",

abstract = "[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (CnF2n+1I+OH{multiset union}-OSO2R, n = 3, 4, 6; R = p-CH3C6H4, CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH or Me3SiOTf. These compounds react with trimethylsilyl derivatives of aromatic compounds under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.",

author = "Viktor Zhdankin and Chris Kuehl",

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doi = "10.1016/S0040-4039(00)73166-2",

language = "English (US)",

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journal = "Tetrahedron Letters",

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AU - Zhdankin, Viktor

AU - Kuehl, Chris

PY - 1994/3/21

Y1 - 1994/3/21

N2 - [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (CnF2n+1I+OH{multiset union}-OSO2R, n = 3, 4, 6; R = p-CH3C6H4, CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH or Me3SiOTf. These compounds react with trimethylsilyl derivatives of aromatic compounds under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

AB - [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (CnF2n+1I+OH{multiset union}-OSO2R, n = 3, 4, 6; R = p-CH3C6H4, CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with pertrifluoroacetic acid and subsequent reaction with TsOH or Me3SiOTf. These compounds react with trimethylsilyl derivatives of aromatic compounds under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

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[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes - new hypervalent iodine species and promising reagents for organic synthesis

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