Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species |
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| Authors: | Mekhman S. Yusubov Viktor V. Zhdankin |
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| Affiliation: | a Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, USA
b Siberian State Medical University and Tomsk Polytechnic University, 2 Moskovsky trakt, 634050 Tomsk, Russia |
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| Abstract: | Several transition metal-mediated oxidations using hypervalent iodine species are reported. A convenient procedure for preparation of iodylarenes via RuCl3-catalyzed oxidation of iodoarenes has been developed. This procedure allows the generation of highly reactive monomeric iodine(V) species, which are excellent oxidants toward alcohols and hydrocarbons in situ. A broad range of substrates can be oxidized to carbonyl compounds by a tandem catalytic system based on the Ru(III)-catalyzed reoxidation of ArIO to ArIO2 using Oxone® as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)3SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes. |
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| Keywords: | Hypervalent iodine Oxidation Catalysis Ruthenium Porphyrins |
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