m-Iodosylbenzoic
Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the
Synthesis of α-Iodo Ketones by Oxidative Iodination of
Ketones

Mehman S. Yusubov; Rosa Y. Yusubova; Tatyana V. Funk; Ki-Whan Chi; Andreas Kirschning; Viktor V. Zhdankin

doi:10.1055/s-0030-1258223

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Synthesis 2010(21): 3681-3685
DOI: 10.1055/s-0030-1258223

PAPER

m-Iodosylbenzoic Acid as a Convenient Recyclable Hypervalent Iodine Oxidant for the Synthesis of α-Iodo Ketones by Oxidative Iodination of Ketones

Mehman S. Yusubov*^a, Rosa Y. Yusubova^a, Tatyana V. Funk^a, Ki-Whan Chi^b, Andreas Kirschning^c, Viktor V. Zhdankin*^d
^a The Siberian State Medical University and Tomsk Polytechnic University, 2 Moskovsky trakt, 634050 Tomsk, Russian Federation
e-Mail: yusubov@mail.ru;
^b University of Ulsan, 680-749 Ulsan, Republic of Korea
^c Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1b, 30167 Hannover, Germany
^d Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Fax: +1(218)7267394; e-Mail: vzhdanki@d.umn.edu;

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Publikationsverlauf

Received 9 June 2010
Publikationsdatum:
20. August 2010 (online)

Abstract
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Abstract

A convenient procedure for the preparation of α-iodo ketones by oxidative iodination of ketones using iodine and m-iodosylbenzoic acid as a recyclable hypervalent iodine oxidant is reported. Various ketones and β-dicarbonyl compounds can be iodinated by this reagent system under mild conditions affording the respective α-iodo-substituted carbonyl compounds in excellent yields. The final products of iodination are conveniently separated from byproducts by simple treatment with anionic exchange resin Amberlite IRA 900 HCO₃ ^- and are isolated with good purity after evaporation of the solvent. The reduced form of the hypervalent iodine oxidant, m-iodobenzoic acid, can be recovered in 91-95% yield from the Amberlite resin by treatment with aqueous hydrochloric acid followed by extraction with ethyl acetate.

Key words

halogenation - iodine - ketones - iodosylbenzene - m-iodosylbenzoic acid - hypervalent iodine

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