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

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

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51 Citations (Scopus)

Abstract

(Chemical Equation Presented) Mechanistic studies of the aromatic hydroxylation by high-valent iron(IV)-oxo porphyrin π-cation radicals revealed that the aromatic oxidation involves an initial electrophilic attack on the π-system of the aromatic ring to produce a tetrahedral radical or cationic σ-complex. The mechanism was proposed on the basis of experimental results such as a large negative Hammett ρ 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.

Original languageEnglish
Pages (from-to)6301-6304
Number of pages4
JournalJournal of Organic Chemistry
Volume72
Issue number16
DOIs
Publication statusPublished - 2007 Aug 1

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ASJC Scopus subject areas

  • Organic Chemistry

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