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Issue 8, 2015
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Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products

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Abstract

An efficient synthesis of 3-fluoroterrylene, a promising molecular nanoprobe for single electron optical sensing, is described. The key synthetic steps comprised the palladium-catalysed cross-coupling reaction of 3-bromoperylene and 4-fluoronaphthalene-1-boronic acid pinacol ester to give 3-(4-fluoronaphthalen-1-yl)perylene, followed by oxidative cyclodehydrogenation to give selectively either 3-fluoroterrylene or its isomer 10-fluorobenzo[4,5]indeno[1,2,3-cd]perylene. The selectivity of the Scholl oxidation under AlCl3/chlorobenzene or DDQ/TfOH conditions was confirmed by 19F NMR.

Graphical abstract: Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products

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Supplementary files

Article information


Submitted
01 Apr 2015
Accepted
15 Jun 2015
First published
16 Jun 2015

New J. Chem., 2015,39, 6498-6503
Article type
Paper
Author version available

Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products

M. S. Markoulides, C. Venturini, D. Neumeyer and A. Gourdon, New J. Chem., 2015, 39, 6498
DOI: 10.1039/C5NJ00808E

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