Jump to main content
Jump to site search

Issue 8, 2015
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 01 Apr 2015, accepted on 15 Jun 2015 and first published on 16 Jun 2015


Article type: Paper
DOI: 10.1039/C5NJ00808E
Author version
available:
Download author version (PDF)
Citation: New J. Chem., 2015,39, 6498-6503
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements