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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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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
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author Castillo, Juan-Carlos
Bravo, Nestor-Fabian
Tamayo, Lenka-Victoria
Mestizo, Paula-Daniela
Hurtado, John
Macías, Mario
Portilla, Jaime
author_facet Castillo, Juan-Carlos
Bravo, Nestor-Fabian
Tamayo, Lenka-Victoria
Mestizo, Paula-Daniela
Hurtado, John
Macías, Mario
Portilla, Jaime
author_sort Castillo, Juan-Carlos
collection PubMed
description [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.
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spelling pubmed-76898932020-11-27 Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction Castillo, Juan-Carlos Bravo, Nestor-Fabian Tamayo, Lenka-Victoria Mestizo, Paula-Daniela Hurtado, John Macías, Mario Portilla, Jaime ACS Omega [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. American Chemical Society 2020-11-12 /pmc/articles/PMC7689893/ /pubmed/33251449 http://dx.doi.org/10.1021/acsomega.0c04592 Text en © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Castillo, Juan-Carlos
Bravo, Nestor-Fabian
Tamayo, Lenka-Victoria
Mestizo, Paula-Daniela
Hurtado, John
Macías, Mario
Portilla, Jaime
Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title_full Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title_fullStr Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title_full_unstemmed Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title_short Water-Compatible Synthesis of 1,2,3-Triazoles under Ultrasonic Conditions by a Cu(I) Complex-Mediated Click Reaction
title_sort water-compatible synthesis of 1,2,3-triazoles under ultrasonic conditions by a cu(i) complex-mediated click reaction
url 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
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