New routes to Cu(l)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles

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Title: New routes to Cu(l)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles
Authors: Abdulkin, Pavel | Moglie, Yanina | Knappett, Benjamin R. | Jefferson, David A. | Yus, Miguel | Alonso, Francisco | Wheatley, Andrew E.H.
Research Group/s: Nuevas Metodologías en Síntesis Orgánica
Center, Department or Service: Universidad de Alicante. Departamento de Departamento de Química Orgánica
Keywords: Nanocatalysts | Synthesis
Knowledge Area: Química Orgánica
Issue Date: 5-Nov-2012
Publisher: Royal Society of Chemistry
Citation: ABDULKIN, Pavel, et al. “New routes to Cu(l)/Cu nanocatalysts for the multicomponent click synthesis of 1,2,3-triazoles”. Nanoscale. Vol. 5, Issue 1 (2012). ISSN 2040-3364, pp. 342-350
Abstract: An array of copper and copper–zinc based nanoparticles (NPs) have been fabricated employing a variety of polymeric capping agents. Analysis by TEM, XRPD and XPS suggests that by manipulating reagent, reductant and solvent conditions it is possible to achieve materials that are mono-/narrow disperse with mean particle sizes in the ≤10 nm regime. Oxidative stability in air is achieved for monometallic NPs using poly(methyl methacrylate) (PMMA) anti-agglomerant in conjunction with a variety of reducing conditions. In contrast, those encapsulated by either poly(1-vinylpyrrolidin-2-one) (PVP) or poly(4-vinylpyridine) (PVPy) rapidly show Cu2O formation, with all data suggesting progressive oxidation from Cu to Cu@Cu2O core–shell structure and finally Cu2O. Bimetallic copper–zinc systems, reveal metal segregation and the formation of Cu2O and ZnO. Catalysts have been screened in the synthesis of 1,2,3-triazoles through multicomponent azide–alkyne 1,3-dipolar cycloaddition. Whereas PMMA- and PVPy-coating results in reduced catalytic activity, those protected by PVP are highly active, with quantitative triazole syntheses achieved at room temperature and with catalyst loadings of 0.03 mol% metal for Cu and CuZn systems prepared using NaH2PO2, N2H4 or NaBH4 reductants.
Sponsor: This work was generously supported by the Spanish Ministerio de Ciencia e Innovación (MICINN; CTQ2007-65218 and Consolider Ingenio 2010-CSD2007-00006), the Generalitat Valenciana (GV; PROMETEO/2009/039), and FEDER. Y. M. and B. R. K. thank the ISO of the Universidad de Alicante, the UK EPSRC and the University of Cambridge for grants.
ISSN: 2040-3364 (Print) | 2040-3372 (Online)
DOI: 10.1039/C2NR32570E
Language: eng
Type: info:eu-repo/semantics/article
Peer Review: si
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