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.
Bibliographical noteFunding Information:
This research was supported by the Korea Science and Engineering Foundation (R03-2001-00028 to W.N. and R05-2000-0008 to R.S.), the Korea Research Foundation (DP0270), and Ewha Womans University (2000).
- Iodobenzene diacetate
- Iron(III) porphyrin