Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis
- 18 May 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 27,p. 3996-4015
- https://doi.org/10.1039/b901221d
Abstract
The oxidation of organic substrates catalyzed by metalloporphyrins constitutes a major class of biomimetic oxidation reactions used in modern synthetic chemistry. Ruthenium porphyrins are among the most extensively studied metalloporphyrin oxidation catalysts. This article provides a brief outline of the metalloporphyrin-based oxidation systems and is focused on the oxidation reactions catalyzed by ruthenium porphyrins performed in the author’s laboratory. A series of ruthenium porphyrin catalysts, including those immobilized onto insoluble supports and covalently attached to soluble supports, promote the oxidation of a wide variety of organic substrates such as styrenes, cycloalkenes, α,β-unsaturated ketones, steroids, benzylic hydrocarbons and arenes with 2,6-dichloropyridine-N-oxide or air in up to >99% yields, with high regio-, chemo- and/or stereoselectivity, and with product turnovers of up to 3.0 × 104, demonstrating the potential application of ruthenium porphyrin-based oxidation systems in organic syntheses.Keywords
This publication has 100 references indexed in Scilit:
- β‐Fluorinated Porphyrins and Related Compounds: An OverviewEuropean Journal of Organic Chemistry, 2008
- Hydrocarbon Oxidation by β-Halogenated Dioxoruthenium(VI) Porphyrin Complexes: Effect of Reduction Potential (RuVI/V) and C-H Bond-Dissociation Energy on Rate ConstantsChemistry – A European Journal, 2005
- A Mechanistic Investigation of Alkene Epoxidation by Sterically Encumbered trans-Dioxoruthenium(VI) PorphyrinsThe Journal of Organic Chemistry, 1999
- Enantioselective hydroxylation of benzylic C–H bonds by D4-symmetric chiral oxoruthenium porphyrins†Chemical Communications, 1999
- Catalytic and asymmetric cyclopropanation of styrenes catalysed by ruthenium porphyrin and porphycene complexesChemical Communications, 1997
- Catalytic asymmetric epoxidation with a chiral ruthenium porphyrin and N-oxidesJournal of the Chemical Society, Perkin Transactions 1, 1997
- Four recent studies in cytochrome P450 modelings: A stable iron porphyrin coordinated by a thiolate ligand; a robust ruthenium porphyrin-pyridine N-oxide derivatives system; polypeptide-bound iron porphyrin; application to drug metabolism studiesJournal of Molecular Catalysis A: Chemical, 1996
- Enantioselective catalysis of epoxidation by metalloporphyrins: application to enantioselective synthesisJournal of Molecular Catalysis A: Chemical, 1996
- Heme-Containing OxygenasesChemical Reviews, 1996
- Multicopper Oxidases and OxygenasesChemical Reviews, 1996