Comparison of riboflavin-derived flavinium salts applied to catalytic H2 O2 oxidations

Organic & Biomolecular Chemistry
Takuya SakaiHiroki Iida

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.

References

Feb 24, 2001·Chemistry : a European Journal·A B Minidis, J E Bäckvall
Mar 6, 2003·Journal of the American Chemical Society·Yasushi ImadaShun-Ichi Murahashi
Jul 18, 2003·Chemistry : a European Journal·Sandra Y JonssonJan-E Bäckvall
Jul 19, 2003·The Journal of Organic Chemistry·Auri A LindénJan-E Bäckvall
Jun 25, 2004·Chemical Communications : Chem Comm·Adam ClossonJan-E Bäckvall
Feb 5, 2005·Angewandte Chemie·Yasushi ImadaTakeshi Naota
Oct 20, 2005·Journal of the American Chemical Society·Yasushi ImadaTakeshi Naota
May 6, 2006·The Journal of Organic Chemistry·Auri A LindénJan-E Bäckvall
May 23, 2006·Journal of Biotechnology·W J H van BerkelM W Fraaije
Apr 19, 2007·Chemistry, an Asian Journal·Yasushi ImadaShun-ichi Murahashi
Jul 12, 2007·Chemical Reviews·Feyissa Gadissa Gelalcha
Nov 16, 2007·Langmuir : the ACS Journal of Surfaces and Colloids·Abhijit SahaArun K Nandi
Dec 12, 2007·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yasushi Imada, Takeshi Naota
Nov 4, 2008·The Journal of Organic Chemistry·Christian SmitAdriaan J Minnaard
Jul 9, 2009·Chemical Communications : Chem Comm·Debabrata PatraVincent M Rotello
Aug 18, 2010·Chemical Communications : Chem Comm·Barrie J MarshDavid R Carbery
Nov 4, 2010·The Journal of Physical Chemistry. a·Vincent SichulaKsenija D Glusac
Nov 26, 2010·Organic & Biomolecular Chemistry·Abhijit SahaArun K Nandi
Apr 16, 2011·Chemistry : a European Journal·Yasushi ImadaTakeshi Naota
Sep 1, 2011·Organic & Biomolecular Chemistry·Viktor MojrTomáš Kraus
Sep 9, 2011·Chemical Communications : Chem Comm·Gonzalo de GonzaloMarco W Fraaije
May 17, 2012·Organic Letters·Shuai ChenFrank W Foss
Jul 13, 2012·Organic Letters·Alexander T MurrayDavid R Carbery
Jul 26, 2012·Journal of the American Chemical Society·Mark J PouyJohn T Groves
Aug 1, 2012·Chemical Communications : Chem Comm·Sachin Prakash PatilByeang Hyean Kim
Aug 17, 2012·Journal of the American Chemical Society·Hiroki IidaEiji Yashima
Sep 25, 2012·Nature Chemistry·Ekaterina MirzakulovaKsenija D Glusac
Feb 27, 2014·Organic & Biomolecular Chemistry·Hana KotoučováRadek Cibulka
Mar 14, 2014·Chemistry : a European Journal·Hiroki IidaEiji Yashima
Jul 25, 2014·Chemical Communications : Chem Comm·Shun-Ichi MurahashiKanji Meguro
Feb 5, 2015·Angewandte Chemie·Michael Fuchs, Alois Fürstner
Jun 17, 2015·Organic & Biomolecular Chemistry·H IidaS-I Murahashi
Jun 20, 2015·Angewandte Chemie·Alexander T MurrayDavid R Carbery
Jul 1, 2015·Carbohydrate Research·Stewart R AlexanderAntony J Fairbanks
Feb 24, 2016·Chemical Communications : Chem Comm·Pramod Prasad PoudelKana Yamamoto
Mar 24, 2016·Organic & Biomolecular Chemistry·Alexander T MurrayDavid R Carbery

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Methods Mentioned

BETA
Fluorescence
column chromatography

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