Issue 10, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
24 Jul 2013
Accepted
14 Aug 2013
First published
14 Aug 2013

Green Chem., 2013,15, 2830-2842

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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