Iodobenzene diacetate as an efficient terminal oxidant in iron(III) porphyrin complex-catalyzed oxygenation reactions

Abstract

An electron-deficient iron(III) porphyrin complex associated with iodobenzene diacetate (PhI(OAc)2) afforded high yields of oxygenated products in catalytic oxygenations of olefins and alkanes when the reactions were carried out in the presence of a small amount of water. An oxoiron(IV) porphyrin cation radical intermediate was generated in the reaction of an iron(III) porphyrin complex and PhI(OAc)2. These results demonstrate that PhI(OAc)2, which is soluble in organic media, safe to use, and readily available, is an efficient oxygen atom donor that can be used as a substitute for polymeric iodosylbenzene (PhIO) in metalloporphyrin-mediated oxygenation reactions. © 2002 Elsevier Science B.V. All rights reserved.