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dc.contributor.author
Alonso, Francisco
dc.contributor.author
Arroyo, Adrian
dc.contributor.author
Martín-García, Iris
dc.contributor.author
Moglie, Yanina Fernanda
dc.date.available
2016-03-10T13:38:56Z
dc.date.issued
2015-10
dc.identifier.citation
Alonso, Francisco; Arroyo, Adrian; Martín-García, Iris; Moglie, Yanina Fernanda; Cross-Dehydrogenative Coupling of Tertiary Amines and Terminal Alkynes Catalyzed by Copper Nanoparticles on Zeolite; Wiley; Advanced Synthesis & Catalysis (print); 357; 16-17; 10-2015; 3549-3561
dc.identifier.issn
1615-4150
dc.identifier.uri
http://hdl.handle.net/11336/4719
dc.description.abstract
A wide range of catalysts based on supported copper nanoparticles have been prepared and tested in the cross-dehydrogenative coupling of tertiary amines and terminal alkynes. Copper nanoparticles on zeolite Y were found to be the most effective catalyst in the presence of tert-butyl hydroperoxide as the oxidant. Contrary to the previously reported methodologies involving copper catalysts, reactions have been accomplished without the need of an inert atmosphere and in the absence of solvent, using 1.5 mol% catalyst. A variety of tertiary amines, including aromatic, benzylic and aliphatic ones, have been coupled with both aromatic and aliphatic alkynes to furnish the corresponding propargylamines in moderate-to-excellent yields. The procedure has been successfully scaled-up to 12 mmol with a high conversion (93%). Moreover, the catalyst has been reused in seven cycles maintaining a good performance. Its catalytic activity has been compared with that of an array of commercial copper catalysts, being superior as regards the conversion and minimizing the alkyne homocoupling as a side reaction. The negative filtration test points to a heterogeneous nature of the process. Based on compelling experimental evidence, a novel reaction mechanism has been delineated which outlines the essential role of free radicals and the couple copper(I)/copper(II).
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Cross Dehydrogenative Coupling
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Heterogeneous Catalysis
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Copper Nanoparticles
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Zeolites
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Alkynes
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Amines
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Copper
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Química Orgánica
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Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
Cross-Dehydrogenative Coupling of Tertiary Amines and Terminal Alkynes Catalyzed by Copper Nanoparticles on Zeolite
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2016-03-30 10:35:44.97925-03
dc.journal.volume
357
dc.journal.number
16-17
dc.journal.pagination
3549-3561
dc.journal.pais
Alemania
dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Alonso, Francisco. Universidad de Alicante. Facultad de Ciencias; España
dc.description.fil
Fil: Arroyo, Adrian. Universidad de Alicante. Facultad de Ciencias; España
dc.description.fil
Fil: Martín-García, Iris. Universidad de Alicante. Facultad de Ciencias; España
dc.description.fil
Fil: Moglie, Yanina Fernanda. Universidad Nacional del Sur. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Bahía Blanca. Instituto de Química del Sur; Argentina
dc.journal.title
Advanced Synthesis & Catalysis (print)
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500787/abstract
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/adsc.201500787
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/issn/1615-4150
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