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Updated: Jul 19, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Azide-Assisted Growth of Copper Nanostructures and Their Application as a Carbon Supported Catalyst in Two-Step
Max Roemer1, William Lewis1,2
1School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia.
Abstract:
Copper nanostructures were obtained from the reduction of Cu(I) under mild conditions in ethanol/water using sodium-l-ascorbate and sodium azide while performing an amination reaction. When the halobenzene substrate was reacted in the presence of a bulk carbon black (CB) support, clustered copper sub-micrometer particles (SMPs) and microparticles (MPs) form. The growth conditions of the MPs were optimized, and the supported nanostructures were isolated and characterized by scanning electron microscopy, energy dispersive X-ray spectroscopy, thermogravimetry, and inductively-coupled plasma mass spectrometry. The particles are mobile and supported within the CB matrix and proved to be active catalysts in the azide-alkyne cycloaddition (CuAAC). The catalytic competency of the particles was assessed in a two-step three-component azide-alkyne cycloaddition of benzyl bromide, sodium azide, and phenylacetylene as a model reaction. The reaction conditions were optimized, and the optimized conditions were applied for the synthesis of triazole compounds with varying levels of functionalization. The recyclability of the catalysts was investigated, depletion modes were discussed, and the conditions were fine-tuned to reach good recyclability. This demonstrates the broader applicability of the SMPs/MPs as CuAAC-catalyst and its limitations.
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