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

Research output: Contribution to journalArticlepeer-review

13 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 languageEnglish
Pages (from-to)7461-7469
Number of pages9
JournalTetrahedron
Volume67
Issue number39
DOIs
StatePublished - 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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