Comparison of Riboflavin-Derived Flavinium Salts Applied to Catalytic H2O2 Oxidations

• Sakai, Takuya

• Kumoi, Takuma

• Ishikawa, Tatsuro

• Nitta, Takahiro

• Iida, Hiroki

抄録

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.

収録刊行物

• Organic & Biomolecular Chemistry

  Organic & Biomolecular Chemistry 16 (1621), 3999-4007, 2018-05-30

  Royal Society of Chemistry

キーワード

• Organic Chemistry
• Physical and Theoretical Chemistry
• Biochemistry

詳細情報

• CRID: 1050283688739361536
• NII論文ID: 120006813711
• ISSN: 14770520
• ISSN: 14770539
• DOI: 10.1039/c8ob00856f
• Web Site: http://ir.lib.shimane-u.ac.jp/49158
• Web Site: http://pubs.rsc.org/en/content/articlepdf/2018/OB/C8OB00856F
• 本文言語コード: en
• 資料種別: journal article
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