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

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.