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

A new monophosphine Cu­(I) complex bearing bis(pyrazolyl)­methane (L 1 ) (CuIL 1 PPh 3 ) 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...

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Bibliographic Details
Published in:ACS omega 2020-11, Vol.5 (46), p.30148-30159
Main Authors: Castillo, Juan-Carlos, Bravo, Nestor-Fabian, Tamayo, Lenka-Victoria, Mestizo, Paula-Daniela, Hurtado, John, Macías, Mario, Portilla, Jaime
Format: Article
Language:English
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Summary:A new monophosphine Cu­(I) complex bearing bis(pyrazolyl)­methane (L 1 ) (CuIL 1 PPh 3 ) 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.
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.0c04592