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Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction

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journal contribution
posted on 12.11.2020, 16:14 by Juan-Carlos Castillo, Nestor-Fabian Bravo, Lenka-Victoria Tamayo, Paula-Daniela Mestizo, John Hurtado, Mario Macías, Jaime Portilla
A new monophosphine Cu­(I) complex bearing bis(pyrazolyl)­methane (L1) (CuIL1PPh3) was synthesized and used as a catalyst for the three-component click reaction from an alkyl halide, sodium azide, and terminal alkyne to furnish 1,4-disubstituted 1,2,3-triazoles in up to 93% yield. The catalyst is highly stable, compatible with oxygen/water, and works with total efficiency under ultrasonic condition. The structure of the complex was studied and confirmed by X-ray crystallography, finding a riveting relationship with its catalytic activity. This sustainable triazoles synthesis is distinguished by its high atom economy, low catalyst loading (up to 0.5 mol %), broad substrate scope, short reaction times, operational simplicity, and an easy gram-scale supply of a functionalized product for subsequent synthetic applications.