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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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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. |
format | Online Article Text |
id | pubmed-7689893 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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