Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of Alkanes

W. Nam, Hee Lim Mi Hee Lim, Kyung Moon Sun Kyung Moon, C. Kim

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121 Scopus citations

Abstract

We have obtained evidence that acylperoxo-iron(III) porphyrin complexes 1a are involved as reactive hydroxylating intermediates in the hydroxylation of alkanes by m-chloroperoxybenzoic acid (m-CPBA) catalyzed by electron-deficient iron(III) porphyrin complexes containing chloride as an anionic axial ligand in a solvent mixture of CH2Cl2 and CH3CN at -40 °C. In addition to the intermediacy of 1a, oxoiron(IV) porphyrin cation radical complexes 2 are formed as the reactive hydroxylating intermediates in the alkane hydroxylations by m-CPBA catalyzed by the iron(III) porphyrin complexes containing triflate (CF3SO3-) as an anionic axial ligand under the same reaction conditions. In line with the recent proposal by Newcomb, Coon, Vaz, and co-workers for cytochrome P-450 reactions, these results suggest that two distinct electrophilic oxidants such as 1a and 2 effect the alkane hydroxylations in iron porphyrin models, depending on the reaction conditions such as the nature of the anionic axial ligands of iron(III) porphyrin complexes.

Original languageEnglish
Pages (from-to)10805-10809
Number of pages5
JournalJournal of the American Chemical Society
Volume122
Issue number44
DOIs
StatePublished - 8 Nov 2000

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