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Updated: May 24, 2026

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of aromatic compounds by catalytic C-C bond activation of biphenylene or angular [3]phenylene
Aleš Korotvička1, Ivana Císařová, Jana Roithová
1Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 128 43 Praha 2, Czech Republic.
Abstract:
Substituted phenanthrenes and picenes were easily prepared by reaction of biphenylene or angular [3]phenylene with various alkynes in the presence of a catalytic amount of [IrCl(cod)](2) /dppe (cod=1,5-cyclooctadiene, dppe=1,2-bis(diphenylphosphino)ethane). The reaction is based on C-C bond activation of the cyclobutane ring. The reaction tolerates the presence of bulky groups on the alkyne, such as the ferrocene moiety. In addition, a catalytic system based on [RhCl(cod)](2)/dppe enabled the, hitherto unreported, reaction of biphenylene with nitriles to provide phenanthridines.
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