4.4 Article

Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO(2)/NaI/HCl system

Journal

TETRAHEDRON
Volume 64, Issue 1, Pages 234-239

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2007.10.062

Keywords

activated aromatic; nitrogenous heterocycles; sodium chlorite; mild iodination

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NaClO(2)/NaI in the presence of HCl is a mild, cheap, and non-toxic reagent for the iodination of phenols, including estradiol and naphthol, aromatic amines, and heterocyclic substrates, e.g., indoles, 8-hydroxyquinoline, imidazole, in fair to excellent yields by a very simple isolation protocol. The scope of the procedure is exemplified by the first iodination of 5-nitroindole to 3-iodo-5-nitroindole in 75% yield. (c) 2007 Elsevier Ltd. All rights reserved.

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