Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides

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Title: Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides
Authors: Alonso, Francisco | Moglie, Yanina | Radivoy, Gabriel | Yus, Miguel
Research Group/s: Nuevas Metodologías en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica | Universidad Nacional del Sur (Bahía Blanca, Argentina). Departamento de Química
Keywords: Click chemistry | Cycloaddition | Alkynes | Azides | Copper | Nanoparticles
Knowledge Area: Química Orgánica
Date Created: 2010
Issue Date: 24-Feb-2010
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Citation: ALONSO VALDÉS, Francisco, et al. "Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides". European Journal of Organic Chemistry. Vol. 2010, Issue 10 (Apr. 2010). ISSN 1434-193X, pp. 1875-1884
Abstract: Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.
Sponsor: Spanish Ministerio de Educación y Ciencia (MEC) (grant no. CTQ2007-65218 and Consolider Ingenio 2010-CSD2007-00006), the Generalitat Valenciana (grant no. PROMETEO/2009/039) and the Secretaría General de Ciencia y Tecnología (SeCyT), Universidad Nacional del Sur (PGI 24/Q014).
URI: http://hdl.handle.net/10045/13870
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.200901446
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.200901446
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