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Synlett 2006(7): 1195-1199  
DOI: 10.1055/s-2006-926374
PAPER
© Georg Thieme Verlag Stuttgart · New York

Oxidative Iodination of Deactivated Arenes in Concentrated Sulfuric Acid with I2/NaIO4 and KI/NaIO4 Iodinating Systems [1]

Lukasz Kraszkiewicz, Maciej Sosnowski, Lech Skulski*
Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, Poland
Fax: +48(22)5720643; e-Mail: lechskulski@yahoo.com;
Further Information

Publication History

Received 17 October 2005
Publication Date:
08 March 2006 (online)

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Abstract

Deactivated arenes were mono- or diiodinated with strong electrophilic I+ reagents, which were prepared from NaIO4 and either I2 or KI in concentrated H2SO4 (minimum 95% by weight). In general a small excess of the dark brown iodinating solution was used (1.1/1.5 equivalents, for nitrobenzene two equivalents was required). The iodinations were conducted at 25-30 °C with a reaction time of 1-2 hours using either a ‘direct’ or an ‘inverse’ method of aromatic iodination to give mono- or diiodinated pure products in 31-91% optimized yields.

Key words

iodoarenes - deactivated arenes - iodine - potassium iodide - sodium periodate - direct oxidative iodination

1

These results were partly presented at the 8th International Electronic Conference on Synthetic Organic Chemistry, paper A024, November 1-30, 2004.

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1

These results were partly presented at the 8th International Electronic Conference on Synthetic Organic Chemistry, paper A024, November 1-30, 2004.