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Synfacts 2008(2): 0217-0217  
DOI: 10.1055/s-2007-992512
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Tagged Hypervalent Iodine Reagents

Contributor(s): Yasuhiro Uozumi, Hiroe Takenaka
E. Kunst, F. Gallier, G. Dujardin, M. S. Yusubov, A. Kirschning*
Leibniz University Hannover, Germany; Université du Maine, Le Mans, France; The Siberian State Medical University and The Tomsk Polytechnic University, Tomsk, Russia
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Aryl iodine(III) reagents bearing a sulfonate tag were prepared and used in the ruthenium-catalyzed alcohol oxidation as oxidant. Thus, the oxidations of various alcohols were carried out with 0.5 mol% of RuCl3 and 1.5-3.2 equiv of the tagged iodine(III) reagent in aqueous acetonitrile at r.t. to give the corresponding ketones (or carboxylic acids) in high yield. The reaction mixture was treated with polymeric ammonium azide (ion-exchange resin) at 100 °C under microwave conditions to scavenge the unreacted iodine(III) and reacted iodine(I) during which the co-produced isobutylazide was evaporated affording the desired products.