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

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...

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Main Authors: Mitrofanov, Alexander Yu., Murashkina, Arina V., Martín-García, Iris, Alonso, Francisco, Beletskaya, Irina P.
Other Authors: Universidad de Alicante. Departamento de Química Orgánica
Format: info:eu-repo/semantics/article
Language:eng
Published: Royal Society of Chemistry 2017
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Online Access:http://hdl.handle.net/10045/69955
id rua10045-69955
record_format dspace
spelling rua10045-699552018-08-17T08:07:02Z Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles Mitrofanov, Alexander Yu. Murashkina, Arina V. Martín-García, Iris Alonso, Francisco Beletskaya, Irina P. Universidad de Alicante. Departamento de Química Orgánica Universidad de Alicante. Instituto Universitario de Síntesis Orgánica Nuevos Materiales y Catalizadores (MATCAT) Catalyst Copper nanoparticles Carbon–carbon Carbon–sulfur Carbon–nitrogen Química Orgánica 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. 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). 2017-10-06T09:10:26Z 2017-10-06T09:10:26Z 2017-08-16 info:eu-repo/semantics/article Catalysis Science & Technology. 2017, 7: 4401-4412. doi:10.1039/C7CY01343D 2044-4753 (Print) 2044-4761 (Online) http://hdl.handle.net/10045/69955 10.1039/C7CY01343D eng http://dx.doi.org/10.1039/C7CY01343D © The Royal Society of Chemistry 2017 info:eu-repo/semantics/openAccess Royal Society of Chemistry
institution Repositorio RUA
collection DSpace
language eng
topic Catalyst
Copper nanoparticles
Carbon–carbon
Carbon–sulfur
Carbon–nitrogen
Química Orgánica
spellingShingle Catalyst
Copper nanoparticles
Carbon–carbon
Carbon–sulfur
Carbon–nitrogen
Química Orgánica
Mitrofanov, Alexander Yu.
Murashkina, Arina V.
Martín-García, Iris
Alonso, Francisco
Beletskaya, Irina P.
Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
description 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.
author2 Universidad de Alicante. Departamento de Química Orgánica
author_facet Universidad de Alicante. Departamento de Química Orgánica
Mitrofanov, Alexander Yu.
Murashkina, Arina V.
Martín-García, Iris
Alonso, Francisco
Beletskaya, Irina P.
format info:eu-repo/semantics/article
author Mitrofanov, Alexander Yu.
Murashkina, Arina V.
Martín-García, Iris
Alonso, Francisco
Beletskaya, Irina P.
author_sort Mitrofanov, Alexander Yu.
title Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
title_short Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
title_full Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
title_fullStr Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
title_full_unstemmed Formation of C–C, C–S and C–N bonds catalysed by supported copper nanoparticles
title_sort formation of c–c, c–s and c–n bonds catalysed by supported copper nanoparticles
publisher Royal Society of Chemistry
publishDate 2017
url http://hdl.handle.net/10045/69955
_version_ 1653308827607498752
score 14.09242

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