Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

Photochem Photobiol Sci. 2010 Oct 28;9(10):1367-77. doi: 10.1039/c0pp00202j. Epub 2010 Sep 14.

Abstract

We report the photocatalytic oxidation of benzylic carbon atoms under mild conditions using riboflavin tetraacetate as photocatalyst and blue-emitting LEDs (440 nm) as light source. Oxygen is the terminal oxidant and hydrogen peroxide appears as the only byproduct in most cases. The process oxidizes toluene derivatives, stilbenes, styrenes and phenylacetic acids to their corresponding benzaldehydes. A benzyl methyl ether and acylated benzyl amines are oxidized directly to the corresponding methyl ester or benzylimides. The mechanism of the reactions has been investigated and the results indicate that oxygen addition to benzyl radicals is a key step of the oxidation process in the case of phenylacetic acids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Light*
  • Oxidation-Reduction
  • Phenylacetates / chemistry*
  • Riboflavin / analogs & derivatives*
  • Riboflavin / chemistry
  • Styrenes / chemistry*
  • Toluene / chemistry*

Substances

  • Phenylacetates
  • Styrenes
  • 2',3',4',5'-tetraacetylriboflavin
  • Toluene
  • phenylacetic acid
  • Riboflavin