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Issue 10, 2013
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Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones

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Abstract

A practical and robust photo Friedel–Crafts acylation of naphthoquinones is described. Although the reaction proceeds slowly in sunlight, the optimised conditions offer a substantial improvement to those already reported, by the utilisation of a more reliable and practical ‘sun-mimicking’ light source, a less hazardous solvent system (trifluorotoluene) and faster reaction times. Using these conditions, the reaction scope has been expanded to include functionalised aldehyde and naphthoquinone substrates, affording the desired photo-products in acceptable to excellent yields (17–81%). Factors influencing the regiochemistry of the photo Friedel–Crafts reaction on unsymmetrical naphthoquinones have also been investigated.

Graphical abstract: Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones

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Publication details

The article was received on 24 Jul 2013, accepted on 14 Aug 2013 and first published on 14 Aug 2013


Article type: Paper
DOI: 10.1039/C3GC41477A
Citation: Green Chem., 2013,15, 2830-2842
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    Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones

    L. J. Mitchell, W. Lewis and C. J. Moody, Green Chem., 2013, 15, 2830
    DOI: 10.1039/C3GC41477A

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