Oxidative cyclodehydrogenation of a perylene derivative: different reagents give different products?
New Journal of Chemistry Pub Date: 2015-06-16 DOI: 10.1039/C5NJ00808E
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.
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Journal Name：New Journal of Chemistry
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CAS no.: 89640-58-4
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