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Synthesis 2004(11): 1869-1873  
DOI: 10.1055/s-2004-829136
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© Georg Thieme Verlag Stuttgart · New York

Nonmetal-Catalyzed Iodination of Arenes with Iodide and Hydrogen Peroxide

Jernej Iskra*, Stojan Stavber, Marko Zupan
Laboratory for Organic and Bioorganic Chemistry, Jozef Stefan Institute and Faculty of Chemistry and Chemical Technology, , University of Ljubljana, Jamova 39, 1000 Ljubljana, Slovenia
Fax: +386(1)4773811; e-Mail: jernej.iskra@ijs.si;
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Publication History

Received 29 March 2004
Publication Date:
01 July 2004 (online)

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Abstract

Oxidative iodination of arenes was carried out with one equivalent of KI and two equivalents of 30% hydrogen peroxide in MeOH in the presence of strong acid. Reactions of various substituted anisoles, phenols and anilines, as well as mesitylene and uracil, were selective and effective with very good yields of isolated halogenated aromatic molecules.

Key words

iodination - haloperoxidation - hydrogen peroxide - oxidative halogenation - aromatics