Metalloporphyrin-based oxidation systems: from biomimetic reactions to application in organic synthesis.
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, alpha,beta-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 3.0x10(4), demonstrating the potential application of ruthenium porphyrin-based oxidation systems in organic syntheses.
Che
Chi-Ming
CM
Department of Chemistry, Open Laboratory of Chemical Biology, Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong. cmche@hku.hk
Huang
Jie-Sheng
JS
D032701:Biomimetics / Q000379:methods*; D002384:Catalysis; D008665:Metalloporphyrins / Q000737:chemistry*; D009930:Organic Chemicals / Q000138:chemical synthesis*; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction
D008665:Metalloporphyrins; D009930:Organic Chemicals