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Issue 21, 2018
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Comparison of riboflavin-derived flavinium salts applied to catalytic H2O2 oxidations

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Abstract

A series of flavinium salts, 5-ethylisoalloxazinium, 5-ethylalloxazinium, and 1,10-ethylene-bridged alloxazinium triflates, were prepared from commercially available riboflavin. This study presents a comparison between their optical and redox properties, and their catalytic activity in H2O2 oxidations of sulfide, tertiary amine, and cyclobutanone. Reflecting the difference between the π-conjugated ring structures, the flavinium salts displayed very different redox properties, with reduction potentials in the order of: 5-ethylisoalloxazinium > 5-ethylalloxazinium > 1,10-ethylene-bridged alloxazinium. A comparison of their catalytic activity revealed that 5-ethylisoalloxazinium triflate specifically oxidises sulfide and cyclobutanone, and 5-ethylalloxazinium triflate smoothly oxidises tertiary amine. 1,10-Bridged alloxazinium triflate, which can be readily obtained from riboflavin in large quantities, showed moderate catalytic activity for the H2O2 oxidation of sulfide and cyclobutanone.

Graphical abstract: Comparison of riboflavin-derived flavinium salts applied to catalytic H2O2 oxidations

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Publication details

The article was received on 12 Apr 2018, accepted on 08 May 2018 and first published on 09 May 2018


Article type: Paper
DOI: 10.1039/C8OB00856F
Citation: Org. Biomol. Chem., 2018,16, 3999-4007
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    Comparison of riboflavin-derived flavinium salts applied to catalytic H2O2 oxidations

    T. Sakai, T. Kumoi, T. Ishikawa, T. Nitta and H. Iida, Org. Biomol. Chem., 2018, 16, 3999
    DOI: 10.1039/C8OB00856F

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