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Updated: Mar 29, 2026

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
The Janus Face of the X Ligand in the Copper-Catalyzed Azide-Alkyne Cycloaddition
Liqun Jin1, Erik A Romero1, Mohand Melaimi1
1UCSD-CNRS Joint Research Laboratory (UMI 3555), Department of Chemistry and Biochemistry, University of California, San Diego , La Jolla, California 92093-0358, United States.
Abstract:
To understand the effect of the anion (X) in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) catalytic process, the kinetic profiles of the successive steps of the catalytic cycle have been studied by performing stoichiometric reactions using copper complexes LCuX in which L is a cyclic (alkyl)(amino)carbene (CAAC) ligand and X = OTf, Cl, OAc, OPh, or OtBu. Basic ligands favor the metalation step but disfavor the formation of the catalytically active σ,π-bis(copper) acetylide, whereas non-nucleophilic ligands favor the latter but slowly promote the former. We show that acetate is a good compromise, and in addition, it is very efficient in the proto-demetalation step.
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