[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes: New and convenient reagents for the preparation of fluoroalkyl(aryl)iodonium salts

C. J. Kuehl; J. T. Bolz; Viktor Zhdankin

doi:10.1055/s-1995-4428

[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes: New and convenient reagents for the preparation of fluoroalkyl(aryl)iodonium salts

C. J. Kuehl
, J. T. Bolz
, Viktor Zhdankin

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (C(n)F(2n+1) I⁺ OH · ^- OSO₂ R, n = 2,3,4,6,8; R = Me,p-MeC₆H₄,CF₃) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with trifluoroperacetic acid and subsequent reaction with MeSO₂OH, p-MeC₆H₄SO₂OH, or Me₃SiOSO₂CF₃. These compouds react with trimethylsilyl-substituted arenes under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

Original language	English (US)
Pages (from-to)	312-316
Number of pages	5
Journal	Synthesis
Issue number	3
DOIs	https://doi.org/10.1055/s-1995-4428
State	Published - Jan 1 1995

Keywords

[hydroxy(sulfonyloxy)iodo]perfluoroalkanes
iodonium salts
perfluoroalkyl(aryl)iodoniu m salts
perfluoroalkyliodides
polyvalent iodine

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10.1055/s-1995-4428

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title = "[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes: New and convenient reagents for the preparation of fluoroalkyl(aryl)iodonium salts",

abstract = "[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (C(n)F(2n+1) I+ OH · - OSO2 R, n = 2,3,4,6,8; R = Me,p-MeC6H4,CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with trifluoroperacetic acid and subsequent reaction with MeSO2OH, p-MeC6H4SO2OH, or Me3SiOSO2CF3. These compouds react with trimethylsilyl-substituted arenes under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.",

keywords = "[hydroxy(sulfonyloxy)iodo]perfluoroalkanes, iodonium salts, perfluoroalkyl(aryl)iodoniu m salts, perfluoroalkyliodides, polyvalent iodine",

author = "Kuehl, \{C. J.\} and Bolz, \{J. T.\} and Viktor Zhdankin",

year = "1995",

month = jan,

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doi = "10.1055/s-1995-4428",

language = "English (US)",

pages = "312--316",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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T1 - [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes

T2 - New and convenient reagents for the preparation of fluoroalkyl(aryl)iodonium salts

AU - Kuehl, C. J.

AU - Bolz, J. T.

AU - Zhdankin, Viktor

PY - 1995/1/1

Y1 - 1995/1/1

N2 - [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (C(n)F(2n+1) I+ OH · - OSO2 R, n = 2,3,4,6,8; R = Me,p-MeC6H4,CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with trifluoroperacetic acid and subsequent reaction with MeSO2OH, p-MeC6H4SO2OH, or Me3SiOSO2CF3. These compouds react with trimethylsilyl-substituted arenes under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

AB - [Hydroxy(sulfonyloxy)iodo]perfluoroalkanes (C(n)F(2n+1) I+ OH · - OSO2 R, n = 2,3,4,6,8; R = Me,p-MeC6H4,CF3) can be prepared in two steps from the corresponding perfluoroalkyliodides by oxidation with trifluoroperacetic acid and subsequent reaction with MeSO2OH, p-MeC6H4SO2OH, or Me3SiOSO2CF3. These compouds react with trimethylsilyl-substituted arenes under mild conditions forming the corresponding perfluoroalkyl(aryl)iodonium salts in good yield.

KW - [hydroxy(sulfonyloxy)iodo]perfluoroalkanes

KW - iodonium salts

KW - perfluoroalkyl(aryl)iodoniu m salts

KW - perfluoroalkyliodides

KW - polyvalent iodine

UR - https://www.scopus.com/pages/publications/0028937948

UR - https://www.scopus.com/pages/publications/0028937948#tab=citedBy

U2 - 10.1055/s-1995-4428

DO - 10.1055/s-1995-4428

M3 - Article

AN - SCOPUS:0028937948

SN - 0039-7881

SP - 312

EP - 316

JO - Synthesis

JF - Synthesis

IS - 3

ER -

[Hydroxy(sulfonyloxy)iodo]perfluoroalkanes: New and convenient reagents for the preparation of fluoroalkyl(aryl)iodonium salts

Abstract

Keywords

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