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

[Image: see text] 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% yie...

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Detalles Bibliográficos
Autores principales: Castillo, Juan-Carlos, Bravo, Nestor-Fabian, Tamayo, Lenka-Victoria, Mestizo, Paula-Daniela, Hurtado, John, Macías, Mario, Portilla, Jaime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7689893/
https://www.ncbi.nlm.nih.gov/pubmed/33251449
http://dx.doi.org/10.1021/acsomega.0c04592
Descripción
Sumario:[Image: see text] 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.