Blue Light District: Sulfide Photooxidation

  • ChemPubSoc Europe Logo
  • Author: Lois O'Leary
  • Published Date: 21 May 2012
  • Source / Publisher: ChemCatChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Blue Light District: Sulfide Photooxidation

Related Societies

The oxidation of sulfides to sulfoxides, which are biologically active compounds in pharmaceuticals and important intermediates in organic synthesis, requires mild methods to avoid overoxidation to sulfones. Radek Cibulka and co-workers, Institute of Chemical Technology, Prague, Czech Republic, use flavins as efficient chemoselective sensitizers to photooxidize sulfides to sulfoxides.

Six 220 mW light-emitting diodes (LEDs) emitted blue light that irradiated the sulfide and tetra-O-acetylriboflavin catalyst. A range of alkyl, alkenyl, and aromatic sulfides, including sterically hindered substrates, were oxidized with quantitative conversions, molar yields up to 100 %, and quantum yields up to 0.7. The reaction proceeds under O2 at room temperature with low catalyst loading (2 mol %). The presence of water in the 95 % ethanol solvent increased the rate of photooxidation for several structurally different sulfides.

Flavins typically operate through an electron transfer mechanism, however, they are thought to mediate the photooxidation by a singlet oxygen mechanism. Structural modifications to improve the stability of the flavin catalyst are currently under investigation.

Article Views: 3985

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

A product of ChemPubSoc Europe (16 European Chemical Societies)and Wiley-VCH