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Updated: Apr 6, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Au-iClick mirrors the mechanism of copper catalyzed azide-alkyne cycloaddition (CuAAC)
Andrew R Powers1, Ion Ghiviriga, Khalil A Abboud
1Department of Chemistry, Center for Catalysis, University of Florida, Gainesville, FL 32611, USA. veige@chem.ufl.edu.
Abstract:
This report outlines the investigation of the iClick mechanism between gold(i)-azides and gold(i)-acetylides to yield digold triazolates. Isolation of digold triazolate complexes offer compelling support for the role of two copper(i) ions in CuAAC. In addition, a kinetic investigation reveals the reaction is first order in both Au(i)-N3 and Au(i)-C[triple bond, length as m-dash]C-R, thus second order overall. A Hammett plot with a ρ = 1.02(5) signifies electron-withdrawing groups accelerate the cycloaddition by facilitating the coordination of the second gold ion in a π-complex. Rate inhibition by the addition of free triphenylphosphine to the reaction indicates that ligand dissociation is a prerequisite for the reaction. The mechanistic conclusions mirror those proposed for the CuAAC reaction.
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