Regioselective iodination of chlorinated aromatic compounds using silver salts

Sudhir N. Joshi; Sandhya M. Vyas; Huimin Wu; Michael W. Duffel; Sean Parkin; Hans Joachim Lehmler

doi:10.1016/j.tet.2011.07.064

Regioselective iodination of chlorinated aromatic compounds using silver salts

Sudhir N. Joshi, Sandhya M. Vyas, Huimin Wu, Michael W. Duffel, Sean Parkin, Hans Joachim Lehmler

Chemistry

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

15 Scopus citations

Abstract

The iodination of chlorinated aromatic compounds using Ag ₂SO₄/I₂, AgSbF₆/I₂, AgBF₄/I₂, and AgPF₆/I₂ offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles, and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para, and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF₆/I₂, AgBF₄/I₂, and AgPF ₆/I₂, but not Ag₂SO₄/I₂, selectively introduced the iodine in para position to the chlorine substituent.

Original language	English
Pages (from-to)	7461-7469
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	39
DOIs	https://doi.org/10.1016/j.tet.2011.07.064
State	Published - Sep 30 2011

Bibliographical note

Funding Information:
This research was supported by grants ES05605 , ES013661 , and ES017425 from the National Institute of Environmental Health Sciences (NIEHS), National Institutes of Health (NIH). Contents of this manuscript are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS/NIH.

Keywords

3-Chlorotoluene
Aniline
Anisole
Chlorobenzene
Non-coordinating ions
Phenol
Silver hexafluoroantimonate
Silver hexafluorophosphate
Silver sulfate
Silver tetrafluoroborate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Regioselective iodination of chlorinated aromatic compounds using silver salts",

abstract = "The iodination of chlorinated aromatic compounds using Ag 2SO4/I2, AgSbF6/I2, AgBF4/I2, and AgPF6/I2 offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles, and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para, and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF6/I2, AgBF4/I2, and AgPF 6/I2, but not Ag2SO4/I2, selectively introduced the iodine in para position to the chlorine substituent.",

keywords = "3-Chlorotoluene, Aniline, Anisole, Chlorobenzene, Non-coordinating ions, Phenol, Silver hexafluoroantimonate, Silver hexafluorophosphate, Silver sulfate, Silver tetrafluoroborate",

author = "Joshi, {Sudhir N.} and Vyas, {Sandhya M.} and Huimin Wu and Duffel, {Michael W.} and Sean Parkin and Lehmler, {Hans Joachim}",

note = "Funding Information: This research was supported by grants ES05605 , ES013661 , and ES017425 from the National Institute of Environmental Health Sciences (NIEHS), National Institutes of Health (NIH). Contents of this manuscript are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS/NIH. ",

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AU - Vyas, Sandhya M.

AU - Wu, Huimin

AU - Duffel, Michael W.

AU - Parkin, Sean

AU - Lehmler, Hans Joachim

N1 - Funding Information: This research was supported by grants ES05605 , ES013661 , and ES017425 from the National Institute of Environmental Health Sciences (NIEHS), National Institutes of Health (NIH). Contents of this manuscript are solely the responsibility of the authors and do not necessarily represent the official views of the NIEHS/NIH.

PY - 2011/9/30

Y1 - 2011/9/30

N2 - The iodination of chlorinated aromatic compounds using Ag 2SO4/I2, AgSbF6/I2, AgBF4/I2, and AgPF6/I2 offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles, and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para, and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF6/I2, AgBF4/I2, and AgPF 6/I2, but not Ag2SO4/I2, selectively introduced the iodine in para position to the chlorine substituent.

AB - The iodination of chlorinated aromatic compounds using Ag 2SO4/I2, AgSbF6/I2, AgBF4/I2, and AgPF6/I2 offers access to iodoarenes that are valuable intermediates in organic synthesis. Specifically, iodination of phenols, anisoles, and anilines with a 3,5-dichloro substitution pattern preferentially yielded the ortho, para, and para iodinated product, respectively. In the case of chlorobenzene and 3-chlorotoluene, AgSbF6/I2, AgBF4/I2, and AgPF 6/I2, but not Ag2SO4/I2, selectively introduced the iodine in para position to the chlorine substituent.

KW - 3-Chlorotoluene

KW - Aniline

KW - Anisole

KW - Chlorobenzene

KW - Non-coordinating ions

KW - Phenol

KW - Silver hexafluoroantimonate

KW - Silver hexafluorophosphate

KW - Silver sulfate

KW - Silver tetrafluoroborate

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JO - Tetrahedron

JF - Tetrahedron

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Regioselective iodination of chlorinated aromatic compounds using silver salts

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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