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N‐Heterocyclic Imine‐Supported Bimetallic Cu(II) Catalyst for Azide‐Alkyne Cycloaddition: Solvent‐free, Reductant‐free, ppm‐level Catalysis to Access 1,4‐Disubstituted Triazoles

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A bimetallic paddle wheel copper(II) complex [Cu2(OAc)4(PriPrNH)2] efficiently catalyzes the click reaction of a variety of azides and alkynes under neat circumstances at a very low catalyst loading, to afford the corresponding 1,4-disubstituted 1,2,3-triazole derivatives quantitatively.


In this article, we present a unique bimetallic paddle wheel copper(II) complex with the molecular formula [Cu2C42H54N6O8]. Several characterization tools have been employed to analyze this complex including single-crystal X-ray diffraction, HRMS, FTIR, and UV-vis spectroscopy. This copper(II) complex excels admirably as a catalytic system in parts-per-million level (ppm) loading for the azide-alkyne ‘click’ reaction under solvent-free conditions, allowing for the quantitative conversion of numerous 1,4-disubstituted 1,2,3-triazole. The specially designed coordinated ligand (perimidin-2-imine) in the Cu(II) complex accelerates the reaction rate significantly during the oxidative homocoupling reaction (OHC) and acts as a base for Cu-coordinated alkyne deprotonation. It has been demonstrated that the catalyst loading of 2.5 ppm is adequate to catalyze the cycloaddition of benzyl azide to phenylacetylene, leading to the extremely high turnover number of 120000 and a turnover frequency of 5000 h−1. Synergistic evidence from stoichiometric reactions and experimental results provides insights into the plausible mechanism for the reaction. Each copper atom contributes to the outcome of the proposed reaction, one by bonding to the acetylide and the other by activating the azide as part of a bimetallic synergistic pathway.

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