Abstract
This paper reports a useful method for facile direct syntheses of aromatic methyl esters from methyl aromatics by aerobic photo-oxidation using anthraquinone-2,3-dicarboxylic acid as an organophotocatalyst.
Notes and references
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When the oxidative esterification of 4-tert-butyltoluene (1a) was carried out using CBr4 (0.1 equiv) in EtOH (1 mL) under molecular oxygen irradiated with fluorescent lamps for 24 h, ethyl benzoate (2l) was obtained only in 1% yield with recovered starting material in 72% yield.
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Anthraquinone derivatives absorb visible light, see: UV-vis spectra of anthraquinone derivatives in supporting information.
When the oxidative esterification of 4-tert-butyltoluene (1a) was carried out using CBr4 (0.1 equiv), EtOH (2 mL) in the presence of CF2CO2H (0.3 equiv) under molecular oxygen irradiated with fluorescent lamps for 24 h, ethyl benzoate (2l) was obtained only in 2% yield with recovered starting material in 69% yield.
Primary electron transfer from the toluene derivatives to AQN* is not excluded.
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† Electronic supplementary information (ESI) available. See DOI: reaction was carried out under an Ar atmosphere. 10.1039/c2pp05387j
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Tada, N., Ikebata, Y., Nobuta, T. et al. Direct aerobic photo-oxidative syntheses of aromatic methyl esters from methyl aromatics using anthraquinone-2,3-dicarboxylic acid as organophotocatalyst. Photochem Photobiol Sci 11, 616–619 (2012). https://doi.org/10.1039/c2pp05387j
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DOI: https://doi.org/10.1039/c2pp05387j