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Synthesis 2009(15): 2505-2508  
DOI: 10.1055/s-0029-1216870
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Oligomeric Iodosylbenzene Sulfate: A Convenient Hypervalent Iodine Reagent for Oxidation of Organic Sulfides and Alkenes

Mehman S. Yusubov*a, Rosa Y. Yusubovaa, Tatyana V. Funka, Ki-Whan Chib, Viktor V. Zhdankin*c
a The Siberian State Medical University and Tomsk Polytechnic University, 2 Moskovsky trakt, 634050 Tomsk, Russian Federation
b Department of Chemistry, University of Ulsan, 680-749 Ulsan, Korea
c Department of Chemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
Fax: +218(726)7394.; e-Mail: vzhdanki@d.umn.edu;
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Publikationsverlauf

Received 6 March 2009
Publikationsdatum:
26. Juni 2009 (online)

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Abstract

Oligomeric iodosylbenzene sulfate, (PhIO)3˙SO3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde.

Key words

oxidations - iodine - sulfoxides - iodosylbenzene - (di­acet­oxyiodo)benzene - hypervalent iodine

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