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Mechanistic insight into the aromatic hydroxylation by high-valent Iron(IV)-oxo porphyrin π-cation radical complexes

Cited 60 time in Web of Science Cited 63 time in Scopus
Authors

Kang, Min-Jung; Song, Woon Ju; Han, Ah-Rim; Choi, Young S.; Jang, Ho G.; Nam, Wonwoo

Issue Date
2007-08
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, Vol.72 No.16, pp.6301-6304
Abstract
[GRAPHICS] Mechanistic studies of the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin pi-cation radicals revealed that the aromatic oxidation involves an initial electrophilic attack on the pi-system of the aromatic ring to produce a tetrahedral radical or cationic sigma-complex. The mechanism was proposed on the basis of experimental results such as a large negative Hammett rho value and an inverse kinetic isotope effect. By carrying out isotope labeling studies, the oxygen in oxygenated products was found to derive from the iron-oxo porphyrin intermediates.
ISSN
0022-3263
URI
https://hdl.handle.net/10371/203498
DOI
https://doi.org/10.1021/jo070557y
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  • College of Natural Sciences
  • Department of Chemistry
Research Area Biochemistry, Inorganic, 무기화학, 생화학

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