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.

Faculty of Chemistry ; Adam Mickiewicz University in Poznan Umultowska 89b 61614 Poznan Poland

Institute for Molecules and Materials Radboud University Heyendaalseweg 135 6525 AJ Nijmegen The Netherlands

Institute of Organic Chemistry and Biochemistry Academy of Science of the Czech Republic Flemingovo náměstí 542 2 16610 Prague Czech Republic

Citace poskytuje Crossref.org

Tuning Deazaflavins Towards Highly Potent Reducing Photocatalysts Guided by Mechanistic Understanding - Enhancement of the Key Step by the Internal Heavy Atom Effect

Deazaflavin reductive photocatalysis involves excited semiquinone radicals

Flavinium Catalysed Photooxidation: Detection and Characterization of Elusive Peroxyflavinium Intermediates