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Synthesis 2011(5): 739-744  
DOI: 10.1055/s-0030-1258429
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Superelectrophilic Iodination of Deactivated Arenes with Triiodoisocyanuric Acid

Rodrigo S. da Ribeiro, Pierre M. Esteves*, Marcio C. S. de Mattos*
Instituto de Química, Departamento de Química Orgânica, Universidade Federal do Rio de Janeiro, Cx. Postal 68545, 21945-970, Rio de Janeiro, Brazil
Fax: +55(21)25627256; e-Mail: mmattos@iq.ufrj.br; e-Mail: pesteves@iq.ufrj.br;
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Publication History

Received 9 November 2010
Publication Date:
10 February 2011 (online)

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Abstract

The reaction of triiodoisocyanuric acid (TICA) with deactivated arenes in acidic medium led to the efficient and regioselective formation of the corresponding iodoarenes, in 55-88% isolated yield. The acidity of the medium was found to be the most important factor influencing the electrophilic iodination of weakly nucleophilic substrates by TICA.

Key words

triiodoisocyanuric acid - iodination - deactivated aromatic compound - iodoarene - electrophilic halogenation

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Aldrich Handbook of Fine Chemicals, Aldrich Chemical Co. (available at http://www.sigmaaldrich.com).