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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.

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  1. Institute of Organic Chemistry, University of Regensburg, Universitätsstr., 31, 93040, Regensburg, Germany

    Robert Lechner, Susanne Kümmel & Burkhard König

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  1. Robert Lechner
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Correspondence to Burkhard König.

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Electronic supplementary information (ESI) available: UV-Vis absorption spectra of RFT 1 during the photo-oxidation of 4-methoxytoluene 3a. See DOI: 10.1039/c0pp00202j

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Lechner, R., Kümmel, S. & König, B. Visible light flavin photo-oxidation of methylbenzenes, styrenes and phenylacetic acids. Photochem Photobiol Sci 9, 1367–1377 (2010). https://doi.org/10.1039/c0pp00202j

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