Application of recyclable, polymer-immobilized iodine(III) oxidants in catalytic C-H bond functionalization

This paper describes the palladium-catalyzed oxidative functionalization of arene and alkane C-H bonds using the polymer-immobilized iodine(III) oxidant poly-4-(diacetoxyiodo)styrene (PS-I(OAc)(2)) and its derivatives. These transformations have been applied to a wide range of organic substrates, and typically proceed with excellent levels of regio- and chemoselectivity as well as with high functional group tolerance. In addition, the polymer-immobilized iodine(l) byproducts of these reactions are readily recovered (by precipitation with methanol), reoxidized (with inexpensive peracetic acid), and reused in multiple catalytic transformations without significant loss of reactivity. Variation of the substituents at the iodine(III) center allows the installation of diverse functionalities, including carbon-oxygen, carbon-chlorine, and carbon-carbon bonds. (c) 2006 Elsevier B.V. All rights reserved.