Transition metal-mediated oxidations utilizing monomeric iodosyl- and iodylarene species

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 (R) as oxidant. It was shown that electrophilic iodine(III) species, originating from oligomeric iodosylbenzene sulfate (PhIO)(3)SO3, are efficient oxygenating agents in catalytic oxidation of aromatic hydrocarbons in the presence of metalloporphyrin complexes. (C) 2010 Elsevier Ltd. All rights reserved.