Three-component coupling of aldehydes, amines and alkynes catalyzed by oxidized copper nanoparticles on titania
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http://hdl.handle.net/10045/22590
Títol: | Three-component coupling of aldehydes, amines and alkynes catalyzed by oxidized copper nanoparticles on titania |
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Autors: | Albaladejo Maricó, María José | Alonso, Francisco | Moglie, Yanina | Yus, Miguel |
Grups d'investigació o GITE: | Nuevas Metodologías en Síntesis Orgánica |
Centre, Departament o Servei: | Universidad de Alicante. Departamento de Química Orgánica |
Paraules clau: | Multicomponent reactions | Nanoparticles | Copper | Alkynes | Aldehydes | Amines |
Àrees de coneixement: | Química Orgánica |
Data de creació: | 2012 |
Data de publicació: | 15-de març-2012 |
Editor: | Wiley-VCH Verlag GmbH & Co. KGaA |
Citació bibliogràfica: | ALBALADEJO, María José, et al. "Three-component coupling of aldehydes, amines and alkynes catalyzed by oxidized copper nanoparticles on titania". European Journal of Organic Chemistry. Vol. 2012, Issue 16 (June 2012). ISSN 1434-193X, pp. 3093-3104 |
Resum: | Copper nanoparticles (mainly as Cu2O) on titania have been shown to catalyze the multicomponent synthesis of propargylamines from aldehydes, amines, and alkynes (A3 coupling) effectively at 70 °C under solvent-free conditions. Both aromatic and aliphatic aldehydes and alkynes have been combined with secondary amines to provide a wide range of propargylamines in moderate to excellent yields. Two examples of ketone/amine/alkyne (KA2) coupling are also included. The catalyst is easy to prepare, reusable at a low copper loading (0.5 mol-%), and exhibits higher catalytic activity than some commercially available copper sources. Some mechanistic aspects of the reaction have also been examined, which have unveiled the participation of copper(I) acetylides in a heterogeneous process. |
Patrocinadors: | This work was generously supported by the Spanish Ministerio de Ciencia e Innovación (MICINN) (grant numbers CTQ2007-65218, CTQ2011-24151), Consolider Ingenio (grant number 2010-CSD2007-00006), the Generalitat Valenciana (grant number PROMETEO/2009/039), and Fondos Europeos para el Desarrollo Regional (FEDER). Y. M. and M. J .A. acknowledge the ISO of the Universidad de Alicante for a grant. |
URI: | http://hdl.handle.net/10045/22590 |
ISSN: | 1434-193X (Print) | 1099-0690 (Online) |
DOI: | 10.1002/ejoc.201200090 |
Idioma: | eng |
Tipus: | info:eu-repo/semantics/article |
Drets: | The definitive version is available at www3.interscience.wiley.com |
Revisió científica: | si |
Versió de l'editor: | http://dx.doi.org/10.1002/ejoc.201200090 |
Apareix a la col·lecció: | INV - MESO - Artículos de Revistas INV - MATCAT - Artículos de Revistas INV - SINTAS - Artículos de Revistas |
Arxius per aquest ítem:
Arxiu | Descripció | Tamany | Format | |
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EurJoc Three-Component Coupling of Aldehides, Amines.pdf | Versión revisada (acceso abierto) | 715,85 kB | Adobe PDF | Obrir Vista prèvia |
EurJoc Three-Component Coupling of Aldehides, Amines_final.pdf | Versión final (acceso restringido) | 668,16 kB | Adobe PDF | Obrir Sol·licitar una còpia |
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