Development of novel oxidation reactions in water using hypervalent iodine reagents

Various aqueous oxidation reactions have been developed since economic and environmental concerns encourage the use of water as a reaction medium. Hypervalent iodine compounds have been used extensively in organic synthesis due to not only low toxicity, ready availability, and easy handling, but also reactivities similar to those of heavy metal reagents or anodic oxidation. However, most of the hypervalent iodine oxidation reactions have been carried out only in limited organic solvents because both the solubility and the reactivity of organo-iodine(Ill or V) compounds have remarkably been decreased in water. In this article, we report novel activation methods of hypervalent iodine species in water and their application to the development of environmentally benign oxidation reactions using polymer-supported iodine(III) reagents. Furthermore, these methods enabled us to replace iodine(V) reagents, such as Dess-Martin periodinane (DMP) and o-iodoxybenzoic acid (IBX) with much safer (non-explosive) and commercially available iodine(III) reagents.