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Rhodium-NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes

Bis-silylated dihydroimidazolium salt 1 and monosilylated imidazolium salt 2 are transformed to (NHC)RhCl(COD) complexes 3 and 4, allowing the preparation of hybrid silica materials either by sol-gel or grafting processes. Full characterization of the materials by means of solid state NMR, N-2-sorption measurements, thermogravimetric analysis (TGA) and elemental analysis was followed by evaluation of catalytic activity in the [2+2+2] cycloaddition of alkynes. Excellent yields of the cycloadducts are obtained for up to six consecutive cycles with the grafted material, using simple filtration to recover the catalyst. Both conventional and microwave heating prove effective for the process described

Financial support from the Spanish Ministerio de Ciencia e Innovacion (MICINN) (grant numbers CTQ2011-23121, CTQ2009-07881, CTQ2012-32436, CTQ2011-22649, CSD2007-00006) and by the Generalitat de Catalunya (grant numbers 2009SGR637, 2009SGR1441, and predoctoral grant to M. Fernandez) is acknowledged. M. Ferre thanks the Universitat Autonoma de Barcelona for a predoctoral scholarship

© European Journal of Organic Chemistry, 2014, vol. 28, p. 6242-6251

Wiley-VCH Verlag

Manager: Ministerio de Ciencia e Innovación (Espanya)
Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Author: Fernández Wang, Martí
Ferré Romeu, Meritxell
Pla i Quintana, Anna
Parella Coll, Teodor
Pleixats, Roser
Roglans i Ribas, Anna
Date: 2014
Abstract: Bis-silylated dihydroimidazolium salt 1 and monosilylated imidazolium salt 2 are transformed to (NHC)RhCl(COD) complexes 3 and 4, allowing the preparation of hybrid silica materials either by sol-gel or grafting processes. Full characterization of the materials by means of solid state NMR, N-2-sorption measurements, thermogravimetric analysis (TGA) and elemental analysis was followed by evaluation of catalytic activity in the [2+2+2] cycloaddition of alkynes. Excellent yields of the cycloadducts are obtained for up to six consecutive cycles with the grafted material, using simple filtration to recover the catalyst. Both conventional and microwave heating prove effective for the process described
Financial support from the Spanish Ministerio de Ciencia e Innovacion (MICINN) (grant numbers CTQ2011-23121, CTQ2009-07881, CTQ2012-32436, CTQ2011-22649, CSD2007-00006) and by the Generalitat de Catalunya (grant numbers 2009SGR637, 2009SGR1441, and predoctoral grant to M. Fernandez) is acknowledged. M. Ferre thanks the Universitat Autonoma de Barcelona for a predoctoral scholarship
Format: application/pdf
Citation: 021738
ISSN: 1434-193X (versió paper)
1099-0690 (versió electrònica)
Document access: http://hdl.handle.net/10256/11333
Language: eng
Publisher: Wiley-VCH Verlag
Collection: MICINN/PN 2012-2014/CTQ2011-23121
AGAUR/2009-2014/2009 SGR-637
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201402649
Articles publicats (D-Q)
Is part of: © European Journal of Organic Chemistry, 2014, vol. 28, p. 6242-6251
Rights: Tots els drets reservats
Subject: Catàlisi heterogènia
Heterogeneous catalysis
Catalitzadors de rodi
Rhodium catalyst
Reaccions d’addició
Addition reactions
Rodi
Rhodium
Ciclització (Química)
Ring formation (Chemistry)
Title: Rhodium-NHC Hybrid Silica Materials as Recyclable Catalysts for [2+2+2] Cycloaddition Reactions of Alkynes
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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