Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of alkanes
Cited 86 times inCited 92 times in
- Participation of two distinct hydroxylating intermediates in iron(III) porphyrin complex-catalyzed hydroxylation of alkanes
- Nam, W; Lim, Mi Hee; Moon, SK; Kim, C
- WATER-SOLUBLE METALLOPORPHYRINS; O BOND-CLEAVAGE; IRON PORPHYRIN; COMPOUND-I; REBOUND MECHANISM; CYTOCHROME-P450; REACTIVITY; EPOXIDATION; ENZYMES; LIGAND
- Issue Date
- AMER CHEMICAL SOC
- JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.122, no.44, pp.10805 - 10809
- 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.
- ; Go to Link
- Appears in Collections:
- PHY_Journal Papers
- Files in This Item:
can give you direct access to the published full text of this article. (UNISTARs only)
Show full item record
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.