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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...

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Autores principales: Quivelli, Andrea Francesca, Vitale, Paola, Perna, Filippo Maria, Capriati, Vito
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
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.
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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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