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Pd embedded in chitosan microspheres as tunable soft-materials for Sonogashira cross-coupling in water-ethanol mixture

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Pd embedded in chitosan microspheres as tunable soft-materials for Sonogashira cross-coupling in water-ethanol mixture

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dc.contributor.author Frindy, Sana es_ES
dc.contributor.author Primo Arnau, Ana María es_ES
dc.contributor.author Lahcini, Mohamed es_ES
dc.contributor.author Bousmina, Mosto es_ES
dc.contributor.author García Gómez, Hermenegildo es_ES
dc.contributor.author El Kadib, Abdelkrim es_ES
dc.date.accessioned 2016-06-03T11:54:49Z
dc.date.available 2016-06-03T11:54:49Z
dc.date.issued 2015
dc.identifier.issn 1463-9262
dc.identifier.uri http://hdl.handle.net/10251/65207
dc.description.abstract Easy shaping of chitosan (CS) as porous self-standing nanofibrillar microspheres allows their use as a palladium carrier. Amino-groups on CS enable the modulation of Pd coordination, giving rise to three different support-catalyst interactions: weakly-coordinated Pd-CS in native CS, incarcerated Pd-CS-Glu in cross-linked CS and strongly-ligated Pd-CS-SH, obtained by the introduction of thiol arms in CS. These catalysts efficiently promote Sonogashira cross-coupling of a large library of functional substrates under mild and sustainable conditions (water-ethanol as solvent at 65 degrees C) and stand as recyclable, metal-scavenging catalytic systems. es_ES
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Green Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject HETEROGENEOUS CATALYST es_ES
dc.subject MESOPOROUS SILICA es_ES
dc.subject BOND FORMATION es_ES
dc.subject MIZOROKI-HECK es_ES
dc.subject PALLADIUM es_ES
dc.subject EFFICIENT es_ES
dc.subject ORGANOCATALYST es_ES
dc.subject ORGANOSILICA es_ES
dc.subject COMPLEXES es_ES
dc.subject CHEMISTRY es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Pd embedded in chitosan microspheres as tunable soft-materials for Sonogashira cross-coupling in water-ethanol mixture es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c4gc02175d
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Frindy, S.; Primo Arnau, AM.; Lahcini, M.; Bousmina, M.; García Gómez, H.; El Kadib, A. (2015). Pd embedded in chitosan microspheres as tunable soft-materials for Sonogashira cross-coupling in water-ethanol mixture. Green Chemistry. 17(3):1893-1898. doi:10.1039/c4gc02175d es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c4gc02175d es_ES
dc.description.upvformatpinicio 1893 es_ES
dc.description.upvformatpfin 1898 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 17 es_ES
dc.description.issue 3 es_ES
dc.relation.senia 305146 es_ES
dc.identifier.eissn 1463-9270
dc.description.references Johansson Seechurn, C. C. C., Kitching, M. O., Colacot, T. J., & Snieckus, V. (2012). Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize. Angewandte Chemie International Edition, 51(21), 5062-5085. doi:10.1002/anie.201107017 es_ES
dc.description.references Sehnal, P., Taylor, R. J. K., & Fairlamb, I. J. S. (2010). Emergence of Palladium(IV) Chemistry in Synthesis and Catalysis. Chemical Reviews, 110(2), 824-889. doi:10.1021/cr9003242 es_ES
dc.description.references Torborg, C., & Beller, M. (2009). Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries. Advanced Synthesis & Catalysis, 351(18), 3027-3043. doi:10.1002/adsc.200900587 es_ES
dc.description.references Hartwig, J. F. (2008). Carbon–heteroatom bond formation catalysed by organometallic complexes. Nature, 455(7211), 314-322. doi:10.1038/nature07369 es_ES
dc.description.references Loska, R., Volla, C. M. R., & Vogel, P. (2008). Iron-Catalyzed Mizoroki-Heck Cross-Coupling Reaction with Styrenes. Advanced Synthesis & Catalysis, 350(18), 2859-2864. doi:10.1002/adsc.200800662 es_ES
dc.description.references Sun, C.-L., Li, B.-J., & Shi, Z.-J. (2011). Direct C−H Transformation via Iron Catalysis. Chemical Reviews, 111(3), 1293-1314. doi:10.1021/cr100198w es_ES
dc.description.references Czaplik, W. M., Mayer, M., Cvengroš, J., & von Wangelin, A. J. (2009). Coming of Age: Sustainable Iron-Catalyzed Cross-Coupling Reactions. ChemSusChem, 2(5), 396-417. doi:10.1002/cssc.200900055 es_ES
dc.description.references Fürstner, A., Leitner, A., Méndez, M., & Krause, H. (2002). Iron-Catalyzed Cross-Coupling Reactions. Journal of the American Chemical Society, 124(46), 13856-13863. doi:10.1021/ja027190t es_ES
dc.description.references Barluenga, J., & Valdés, C. (2011). Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions. Angewandte Chemie International Edition, 50(33), 7486-7500. doi:10.1002/anie.201007961 es_ES
dc.description.references Yin, & Liebscher, J. (2007). Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chemical Reviews, 107(1), 133-173. doi:10.1021/cr0505674 es_ES
dc.description.references Phan, N. T. S., Van Der Sluys, M., & Jones, C. W. (2006). On the Nature of the Active Species in Palladium Catalyzed Mizoroki–Heck and Suzuki–Miyaura Couplings – Homogeneous or Heterogeneous Catalysis, A Critical Review. Advanced Synthesis & Catalysis, 348(6), 609-679. doi:10.1002/adsc.200505473 es_ES
dc.description.references Weck, M., & Jones, C. W. (2007). Mizoroki−Heck Coupling Using Immobilized Molecular Precatalysts:  Leaching Active Species from Pd Pincers, Entrapped Pd Salts, and Pd NHC Complexes. Inorganic Chemistry, 46(6), 1865-1875. doi:10.1021/ic061898h es_ES
dc.description.references WEBB, J., MACQUARRIE, S., MCELENEY, K., & CRUDDEN, C. (2007). Mesoporous silica-supported Pd catalysts: An investigation into structure, activity, leaching and heterogeneity. Journal of Catalysis, 252(1), 97-109. doi:10.1016/j.jcat.2007.09.007 es_ES
dc.description.references Garrett, C. E., & Prasad, K. (2004). The Art of Meeting Palladium Specifications in Active Pharmaceutical Ingredients Produced by Pd-Catalyzed Reactions. Advanced Synthesis & Catalysis, 346(8), 889-900. doi:10.1002/adsc.200404071 es_ES
dc.description.references Glasspoole, B. W., Webb, J. D., & Crudden, C. M. (2009). Catalysis with chemically modified mesoporous silicas: Stability of the mesostructure under Suzuki–Miyaura reaction conditions. Journal of Catalysis, 265(2), 148-154. doi:10.1016/j.jcat.2009.04.020 es_ES
dc.description.references Modak, A., Mondal, J., & Bhaumik, A. (2012). Pd-grafted periodic mesoporous organosilica: an efficient heterogeneous catalyst for Hiyama and Sonogashira couplings, and cyanation reactions. Green Chemistry, 14(10), 2840. doi:10.1039/c2gc35820d es_ES
dc.description.references Macquarrie, D. J., & Hardy, J. J. E. (2005). Applications of Functionalized Chitosan in Catalysis†. Industrial & Engineering Chemistry Research, 44(23), 8499-8520. doi:10.1021/ie050007v es_ES
dc.description.references A. El Kadib , ChemSusChem20158217244 es_ES
dc.description.references El Kadib, A., Primo, A., Molvinger, K., Bousmina, M., & Brunel, D. (2011). Nanosized Vanadium, Tungsten and Molybdenum Oxide Clusters Grown in Porous Chitosan Microspheres as Promising Hybrid Materials for Selective Alcohol Oxidation. Chemistry – A European Journal, 17(28), 7940-7946. doi:10.1002/chem.201003740 es_ES
dc.description.references El Kadib, A., & Bousmina, M. (2012). Chitosan Bio-Based Organic-Inorganic Hybrid Aerogel Microspheres. Chemistry - A European Journal, 18(27), 8264-8277. doi:10.1002/chem.201104006 es_ES
dc.description.references Kadib, A. E., Bousmina, M., & Brunel, D. (2014). Recent Progress in Chitosan Bio-Based Soft Nanomaterials. Journal of Nanoscience and Nanotechnology, 14(1), 308-331. doi:10.1166/jnn.2014.9012 es_ES
dc.description.references Primo, A., & Quignard, F. (2010). Chitosan as efficient porous support for dispersion of highly active gold nanoparticles: design of hybrid catalyst for carbon–carbon bond formation. Chemical Communications, 46(30), 5593. doi:10.1039/c0cc01137a es_ES
dc.description.references Valentin, R., Molvinger, K., Quignard, F., & Brunel, D. (2003). Supercritical CO2 dried chitosan: an efficient intrinsic heterogeneous catalyst in fine chemistry. New Journal of Chemistry, 27(12), 1690. doi:10.1039/b310109f es_ES
dc.description.references Primo, A., Atienzar, P., Sanchez, E., Delgado, J. M., & García, H. (2012). From biomass wastes to large-area, high-quality, N-doped graphene: catalyst-free carbonization of chitosan coatings on arbitrary substrates. Chemical Communications, 48(74), 9254. doi:10.1039/c2cc34978g es_ES
dc.description.references Ngah, W. S. W., Ab Ghani, S., & Kamari, A. (2005). Adsorption behaviour of Fe(II) and Fe(III) ions in aqueous solution on chitosan and cross-linked chitosan beads. Bioresource Technology, 96(4), 443-450. doi:10.1016/j.biortech.2004.05.022 es_ES
dc.description.references El Hankari, S., El Kadib, A., Finiels, A., Bouhaouss, A., Moreau, J. J. E., Crudden, C. M., … Hesemann, P. (2011). SBA-15-Type Organosilica with 4-Mercapto-N,N-bis-(3-Si-propyl)butanamide for Palladium Scavenging and Cross-Coupling Catalysis. Chemistry - A European Journal, 17(32), 8984-8994. doi:10.1002/chem.201002190 es_ES
dc.description.references Crudden, C. M., Sateesh, M., & Lewis, R. (2005). Mercaptopropyl-Modified Mesoporous Silica:  A Remarkable Support for the Preparation of a Reusable, Heterogeneous Palladium Catalyst for Coupling Reactions. Journal of the American Chemical Society, 127(28), 10045-10050. doi:10.1021/ja0430954 es_ES
dc.description.references McEleney, K., Crudden, C. M., & Horton, J. H. (2009). X-ray Photoelectron Spectroscopy and the Auger Parameter As Tools for Characterization of Silica-Supported Pd Catalysts for the Suzuki−Miyaura Reaction. The Journal of Physical Chemistry C, 113(5), 1901-1907. doi:10.1021/jp808837k es_ES
dc.description.references Roy, A. S., Mondal, J., Banerjee, B., Mondal, P., Bhaumik, A., & Islam, S. M. (2014). Pd-grafted porous metal–organic framework material as an efficient and reusable heterogeneous catalyst for C–C coupling reactions in water. Applied Catalysis A: General, 469, 320-327. doi:10.1016/j.apcata.2013.10.017 es_ES
dc.description.references Kadib, A. E., Molvinger, K., Cacciaguerra, T., Bousmina, M., & Brunel, D. (2011). Chitosan templated synthesis of porous metal oxide microspheres with filamentary nanostructures. Microporous and Mesoporous Materials, 142(1), 301-307. doi:10.1016/j.micromeso.2010.12.012 es_ES
dc.description.references Kühbeck, D., Saidulu, G., Reddy, K. R., & Díaz, D. D. (2012). Critical assessment of the efficiency of chitosan biohydrogel beads as recyclable and heterogeneous organocatalyst for C–C bond formation. Green Chem., 14(2), 378-392. doi:10.1039/c1gc15925a es_ES
dc.description.references Khalafi-Nezhad, A., & Mohammadi, S. (2014). Chitosan supported ionic liquid: a recyclable wet and dry catalyst for the direct conversion of aldehydes into nitriles and amides under mild conditions. RSC Advances, 4(27), 13782. doi:10.1039/c3ra43440k es_ES
dc.description.references El Kadib, A., McEleney, K., Seki, T., Wood, T. K., & Crudden, C. M. (2011). Cross-Coupling in the Preparation of Pharmaceutically Relevant Substrates using Palladium Supported on Functionalized Mesoporous Silicas. ChemCatChem, 3(8), 1281-1285. doi:10.1002/cctc.201100021 es_ES


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