Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles

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Title: Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
Authors: Mitrofanov, Alexander Yu. | Murashkina, Arina V. | Martín-García, Iris | Alonso, Francisco | Beletskaya, Irina P.
Research Group/s: Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Catalyst | Copper nanoparticles | Carbon–carbon | Carbon–sulfur | Carbon–nitrogen
Knowledge Area: Química Orgánica
Issue Date: 16-Aug-2017
Publisher: Royal Society of Chemistry
Citation: Catalysis Science & Technology. 2017, 7: 4401-4412. doi:10.1039/C7CY01343D
Abstract: Transition-metal catalysed cross-coupling reactions are still dominated by palladium chemistry. Within the recent past, copper has gained ground against palladium by virtue of its cheaper price and equivalent function in certain reactions. Four catalysts consisting of copper nanoparticles on zeolite, titania, montmorillonite and activated carbon have been tested in three palladium- and ligand-free cross-coupling reactions to form carbon–carbon, carbon–sulfur and carbon–nitrogen bonds. CuNPs/zeolite has been found to be the best one in the Sonogashira reaction of aryl iodides and arylacetylenes, as well as in the coupling of aryl halides with aryl and alkyl thiols, being reusable in both cases. However, the arylation of nitrogen-containing heterocycles (imidazole, pyrazole, benzimidazole and indole) has been better accomplished with CuNPs/titania, albeit CuNPs/activated carbon showed better recycling properties. The catalytic activity of the nanostructured catalysts has been compared with that of twelve commercial copper catalysts, with the former outperforming the latter in the three types of reactions studied.
Sponsor: I. P. Beletskaya thanks the Russian Science Foundation (RSF, grant no. 14-23-00186 P) and A. Yu. Mitrofanov thanks the Russian Foundation for Basic Research (grant no. 16-33-60207) for their financial support. This work was also generously supported by the Spanish Ministerio de Economía y Competitividad (MINECO; grant no. CTQ-2015-66624-P) and the Institute of Organic Synthesis (ISO). I. M.-G. thanks the ISO and the Vicerrectorado de Investigación y Transferencia del Conocimiento of the Universidad de Alicante for predoctoral grants (no. UAFPU2016-034).
ISSN: 2044-4753 (Print) | 2044-4761 (Online)
DOI: 10.1039/C7CY01343D
Language: eng
Type: info:eu-repo/semantics/article
Rights: © The Royal Society of Chemistry 2017
Peer Review: si
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Appears in Collections:INV - MATCAT - Artículos de Revistas

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