Combining Flavin Photocatalysis and Organocatalysis: Metal-Free Aerobic Oxidation of Unactivated Benzylic Substrates
Status PubMed-not-MEDLINE Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
We report a system with ethylene-bridged flavinium salt 2b which catalyzes the aerobic oxidation of toluenes and benzyl alcohols with high oxidation potential ( Eox > +2.5 V vs SCE) to give the corresponding benzoic acids under visible light irradiation. This is caused by the high oxidizing power of excited 2b ( E(2b*) = +2.67 V vs SCE) involved in photooxidation and by the accompanying dark organocatalytic oxygenation provided by the in situ formed flavin hydroperoxide 2b-OOH.
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Deazaflavin reductive photocatalysis involves excited semiquinone radicals