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Issue 10, 2010
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Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids

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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.

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

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Article information


Submitted
29 Jun 2010
Accepted
05 Aug 2010
First published
14 Sep 2010

Photochem. Photobiol. Sci., 2010,9, 1367-1377
Article type
Paper

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

R. Lechner, S. Kümmel and B. König, Photochem. Photobiol. Sci., 2010, 9, 1367
DOI: 10.1039/C0PP00202J

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