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Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands
The CuI-catalyzed Ullmann amine cross-coupling between (hetero)aryl halides (Br, I) and aromatic and aliphatic amines has been accomplished in deep eutectic solvents as environmentally benign and recycling reaction media. Under optimized conditions, the reaction proceeds smoothly under mild conditio...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2019
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6833937/ https://www.ncbi.nlm.nih.gov/pubmed/31737602 http://dx.doi.org/10.3389/fchem.2019.00723 |
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author | Quivelli, Andrea Francesca Vitale, Paola Perna, Filippo Maria Capriati, Vito |
author_facet | Quivelli, Andrea Francesca Vitale, Paola Perna, Filippo Maria Capriati, Vito |
author_sort | Quivelli, Andrea Francesca |
collection | PubMed |
description | The CuI-catalyzed Ullmann amine cross-coupling between (hetero)aryl halides (Br, I) and aromatic and aliphatic amines has been accomplished in deep eutectic solvents as environmentally benign and recycling reaction media. Under optimized conditions, the reaction proceeds smoothly under mild conditions (60–100°C) in air, in the absence of ligands, with a catalyst (CuI) loading of 10 mol% and K(2)CO(3) (aliphatic primary and secondary amines) or t-BuOK (aromatic amines) as the base. A variety of amines have been synthesized in yields up to 98% with a broad substrate scope. |
format | Online Article Text |
id | pubmed-6833937 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-68339372019-11-15 Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands Quivelli, Andrea Francesca Vitale, Paola Perna, Filippo Maria Capriati, Vito Front Chem Chemistry The CuI-catalyzed Ullmann amine cross-coupling between (hetero)aryl halides (Br, I) and aromatic and aliphatic amines has been accomplished in deep eutectic solvents as environmentally benign and recycling reaction media. Under optimized conditions, the reaction proceeds smoothly under mild conditions (60–100°C) in air, in the absence of ligands, with a catalyst (CuI) loading of 10 mol% and K(2)CO(3) (aliphatic primary and secondary amines) or t-BuOK (aromatic amines) as the base. A variety of amines have been synthesized in yields up to 98% with a broad substrate scope. Frontiers Media S.A. 2019-10-30 /pmc/articles/PMC6833937/ /pubmed/31737602 http://dx.doi.org/10.3389/fchem.2019.00723 Text en Copyright © 2019 Quivelli, Vitale, Perna and Capriati. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Quivelli, Andrea Francesca Vitale, Paola Perna, Filippo Maria Capriati, Vito Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title | Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title_full | Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title_fullStr | Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title_full_unstemmed | Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title_short | Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C–N Coupling Reactions With No Additional Ligands |
title_sort | reshaping ullmann amine synthesis in deep eutectic solvents: a mild approach for cu-catalyzed c–n coupling reactions with no additional ligands |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6833937/ https://www.ncbi.nlm.nih.gov/pubmed/31737602 http://dx.doi.org/10.3389/fchem.2019.00723 |
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