Three-component coupling of aldehydes, amines and alkynes catalyzed by oxidized copper nanoparticles on titania

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Title: Three-component coupling of aldehydes, amines and alkynes catalyzed by oxidized copper nanoparticles on titania
Authors: Albaladejo Maricó, María José | Alonso, Francisco | Moglie, Yanina | Yus, Miguel
Research Group/s: Nuevas Metodologías en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica
Keywords: Multicomponent reactions | Nanoparticles | Copper | Alkynes | Aldehydes | Amines
Knowledge Area: Química Orgánica
Date Created: 2012
Issue Date: 15-Mar-2012
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: 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
Abstract: 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.
Sponsor: 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
Language: eng
Type: info:eu-repo/semantics/article
Rights: The definitive version is available at www3.interscience.wiley.com
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/ejoc.201200090
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