4.6 Article

An Alternative to the Sandmeyer Approach to Aryl Iodides

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 17, Pages 6394-6398

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201500151

Keywords

aryl iodides; diaryliodonium salt; electrophilic substitution; regioselectivity; Sandmeyer reaction

Funding

  1. Institute of Biomedical Imaging and Bioengineering of the National Institutes of Health [R01 EB015536]
  2. National Natural Science Foundation of China [21202148]

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Iodoarenes are important synthons for a wide range of organic transformations. Here we report a general strategy to prepare singly iodinated electron-rich aromatic compounds through the intermediacy of diaryliodonium salts. This process, which incorporates a phase separation that greatly simplifies product purification, is an attractive replacement for the Sandmeyer approach to iodoarenes that are otherwise difficult to access.

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