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Iridium complexes catalysed the selective dehydrogenation of glucose to gluconic acid in water

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Iridium complexes catalysed the selective dehydrogenation of glucose to gluconic acid in water

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dc.contributor.author Borja, Pilar es_ES
dc.contributor.author Vicent, Cristian es_ES
dc.contributor.author Baya, Miguel es_ES
dc.contributor.author García Gómez, Hermenegildo es_ES
dc.contributor.author Mata, Jose A. es_ES
dc.date.accessioned 2020-06-20T03:30:39Z
dc.date.available 2020-06-20T03:30:39Z
dc.date.issued 2018-09-07 es_ES
dc.identifier.issn 1463-9262 es_ES
dc.identifier.uri http://hdl.handle.net/10251/146716
dc.description.abstract [EN] We describe an unprecedented catalytic dehydrogenation of glucose by homogeneous catalysts. Iridium(iii) complexes containing the fragment [Cp*Ir(NHC)](2+) (NHC = N-heterocyclic carbene ligand) are shown to be very active and highly selective catalysts for the dehydrogenation of glucose to gluconic acid and molecular hydrogen. Glucose is converted to gluconic acid at a catalyst loading of 2 mol%, at reflux in water, without additives and with a selectivity of over 95%. Experimental evidence obtained by H-1 NMR spectroscopy and mass spectrometry (ESI/MS) reveals the formation of iridium coordinated to glucose and gluconic acid species. A plausible mechanism is proposed, based on the experimental evidence and supported by DFT calculations. es_ES
dc.description.sponsorship The authors thank the MINECO (Severo Ochoa, CTQ2015-69153-C2-1-R, CTQ2015-69153-C2-2-R and CTQ2015-67461-P), Diputacion General de Aragon (Grupo Consolidado E21) and Universitat Jaume I (P1.1B2015-09) for financial support. P. Borja thanks the Universitat Jaume I for a postdoctoral grant. The authors are very grateful to the 'Serveis Centrals d'Instrumentacio Cientifica (SCIC)' of the Universitat Jaume I, S. Fuertes (Universidad of Zaragoza) for data collection of the X-ray structure of 4 and to the Instituto de Biocomputacion y Fisica de Sistemas Complejos (BIFI) and the Centro de Supercomputacion de Galicia (CESGA) for the generous allocation of computational resources. es_ES
dc.language Inglés es_ES
dc.publisher The Royal Society of Chemistry es_ES
dc.relation.ispartof Green Chemistry es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Iridium complexes catalysed the selective dehydrogenation of glucose to gluconic acid in water es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c8gc01933a es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2015-69153-C2-2-R/ES/APLICACIONES CATALITICAS DE COMPUESTOS ORGANOMETALICOS INMOVILIZADOS EN LA SUFPERFICIE DE GRAFENOS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2015-67461-P/ES/COMPUESTOS ORGANOMETALICOS IMPLICADOS EN PROCESOS REDOX Y%2FO FOTOINDUCIDOS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/DGA//E21/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/UJI//P1.1B2015-09/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2015-69153-C2-1-R/ES/EXPLOTANDO EL USO DEL GRAFENO EN CATALISIS. USO DEL GRAFENO COMO CARBOCATALIZADOR O COMO SOPORTE/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Borja, P.; Vicent, C.; Baya, M.; García Gómez, H.; Mata, JA. (2018). Iridium complexes catalysed the selective dehydrogenation of glucose to gluconic acid in water. Green Chemistry. 20(17):4094-4101. https://doi.org/10.1039/c8gc01933a es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1039/c8gc01933a es_ES
dc.description.upvformatpinicio 4094 es_ES
dc.description.upvformatpfin 4101 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 20 es_ES
dc.description.issue 17 es_ES
dc.relation.pasarela S\382649 es_ES
dc.contributor.funder Universitat Jaume I es_ES
dc.contributor.funder Diputación General de Aragón es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.description.references Corma, A., Iborra, S., & Velty, A. (2007). Chemical Routes for the Transformation of Biomass into Chemicals. Chemical Reviews, 107(6), 2411-2502. doi:10.1021/cr050989d es_ES
dc.description.references Besson, M., Gallezot, P., & Pinel, C. (2013). Conversion of Biomass into Chemicals over Metal Catalysts. Chemical Reviews, 114(3), 1827-1870. doi:10.1021/cr4002269 es_ES
dc.description.references Sheldon, R. A. (2014). Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem., 16(3), 950-963. doi:10.1039/c3gc41935e es_ES
dc.description.references Mika, L. T., Cséfalvay, E., & Németh, Á. (2017). Catalytic Conversion of Carbohydrates to Initial Platform Chemicals: Chemistry and Sustainability. Chemical Reviews, 118(2), 505-613. doi:10.1021/acs.chemrev.7b00395 es_ES
dc.description.references Climent, M. J., Corma, A., & Iborra, S. (2011). Converting carbohydrates to bulk chemicals and fine chemicals over heterogeneous catalysts. Green Chemistry, 13(3), 520. doi:10.1039/c0gc00639d es_ES
dc.description.references Climent, M. J., Corma, A., & Iborra, S. (2011). Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals. Chemical Reviews, 111(2), 1072-1133. doi:10.1021/cr1002084 es_ES
dc.description.references Gallezot, P. (2012). Conversion of biomass to selected chemical products. Chem. Soc. Rev., 41(4), 1538-1558. doi:10.1039/c1cs15147a es_ES
dc.description.references Makhubela, B. C. E., & Darkwa, J. (2018). The Role of Noble Metal Catalysts in Conversion of Biomass and Bio-derived Intermediates to Fuels and Chemicals. Johnson Matthey Technology Review, 62(1), 4-31. doi:10.1595/205651317x696261 es_ES
dc.description.references Gallezot, P. (2008). Catalytic Conversion of Biomass: Challenges and Issues. ChemSusChem, 1(8-9), 734-737. doi:10.1002/cssc.200800091 es_ES
dc.description.references Geilen, F. M. A., Engendahl, B., Harwardt, A., Marquardt, W., Klankermayer, J., & Leitner, W. (2010). Selective and Flexible Transformation of Biomass-Derived Platform Chemicals by a Multifunctional Catalytic System. Angewandte Chemie International Edition, 49(32), 5510-5514. doi:10.1002/anie.201002060 es_ES
dc.description.references Mirescu, A., Berndt, H., Martin, A., & Prüße, U. (2007). Long-term stability of a 0.45% Au/TiO2 catalyst in the selective oxidation of glucose at optimised reaction conditions. Applied Catalysis A: General, 317(2), 204-209. doi:10.1016/j.apcata.2006.10.016 es_ES
dc.description.references BAATZ, C., & PRUSE, U. (2007). Preparation of gold catalysts for glucose oxidation by incipient wetness. Journal of Catalysis, 249(1), 34-40. doi:10.1016/j.jcat.2007.03.026 es_ES
dc.description.references Önal, Y. (2004). Structure sensitivity and kinetics of ?-glucose oxidation to ?-gluconic acid over carbon-supported gold catalysts. Journal of Catalysis, 223(1), 122-133. doi:10.1016/j.jcat.2004.01.010 es_ES
dc.description.references Biella, S., Prati, L., & Rossi, M. (2002). Selective Oxidation of D-Glucose on Gold Catalyst. Journal of Catalysis, 206(2), 242-247. doi:10.1006/jcat.2001.3497 es_ES
dc.description.references Gallezot, P. (2007). Process options for converting renewable feedstocks to bioproducts. Green Chemistry, 9(4), 295. doi:10.1039/b615413a es_ES
dc.description.references Balaraman, E., Khaskin, E., Leitus, G., & Milstein, D. (2013). Catalytic transformation of alcohols to carboxylic acid salts and H2 using water as the oxygen atom source. Nature Chemistry, 5(2), 122-125. doi:10.1038/nchem.1536 es_ES
dc.description.references Zweifel, T., Naubron, J.-V., & Grützmacher, H. (2009). Catalyzed Dehydrogenative Coupling of Primary Alcohols with Water, Methanol, or Amines. Angewandte Chemie International Edition, 48(3), 559-563. doi:10.1002/anie.200804757 es_ES
dc.description.references Fujita, K., Tamura, R., Tanaka, Y., Yoshida, M., Onoda, M., & Yamaguchi, R. (2017). Dehydrogenative Oxidation of Alcohols in Aqueous Media Catalyzed by a Water-Soluble Dicationic Iridium Complex Bearing a Functional N-Heterocyclic Carbene Ligand without Using Base. ACS Catalysis, 7(10), 7226-7230. doi:10.1021/acscatal.7b02560 es_ES
dc.description.references Brewster, T. P., Ou, W. C., Tran, J. C., Goldberg, K. I., Hanson, S. K., Cundari, T. R., & Heinekey, D. M. (2014). Iridium, Rhodium, and Ruthenium Catalysts for the «Aldehyde–Water Shift» Reaction. ACS Catalysis, 4(9), 3034-3038. doi:10.1021/cs500843a es_ES
dc.description.references Dobereiner, G. E., Yuan, J., Schrock, R. R., Goldman, A. S., & Hackenberg, J. D. (2013). Catalytic Synthesis of n-Alkyl Arenes through Alkyl Group Cross-Metathesis. Journal of the American Chemical Society, 135(34), 12572-12575. doi:10.1021/ja4066392 es_ES
dc.description.references Choi, J., MacArthur, A. H. R., Brookhart, M., & Goldman, A. S. (2011). Dehydrogenation and Related Reactions Catalyzed by Iridium Pincer Complexes. Chemical Reviews, 111(3), 1761-1779. doi:10.1021/cr1003503 es_ES
dc.description.references Wang, C., & Xiao, J. (2017). Iridacycles for hydrogenation and dehydrogenation reactions. Chemical Communications, 53(24), 3399-3411. doi:10.1039/c7cc01103b es_ES
dc.description.references Wang, X., Wang, C., Liu, Y., & Xiao, J. (2016). Acceptorless dehydrogenation and aerobic oxidation of alcohols with a reusable binuclear rhodium(ii) catalyst in water. Green Chemistry, 18(17), 4605-4610. doi:10.1039/c6gc01272h es_ES
dc.description.references Sawama, Y., Morita, K., Yamada, T., Nagata, S., Yabe, Y., Monguchi, Y., & Sajiki, H. (2014). Rhodium-on-carbon catalyzed hydrogen scavenger- and oxidant-free dehydrogenation of alcohols in aqueous media. Green Chemistry, 16(7), 3439. doi:10.1039/c4gc00434e es_ES
dc.description.references Robbins, D. W., & Hartwig, J. F. (2011). A Simple, Multidimensional Approach to High-Throughput Discovery of Catalytic Reactions. Science, 333(6048), 1423-1427. doi:10.1126/science.1207922 es_ES
dc.description.references Da Vià, L., Recchi, C., Davies, T. E., Greeves, N., & Lopez‐Sanchez, J. A. (2016). Visible‐Light‐Controlled Oxidation of Glucose using Titania‐Supported Silver Photocatalysts. ChemCatChem, 8(22), 3475-3483. doi:10.1002/cctc.201600775 es_ES
dc.description.references Da Vià, L., Recchi, C., Gonzalez-Yañez, E. O., Davies, T. E., & Lopez-Sanchez, J. A. (2017). Visible light selective photocatalytic conversion of glucose by TiO2. Applied Catalysis B: Environmental, 202, 281-288. doi:10.1016/j.apcatb.2016.08.035 es_ES
dc.description.references Monge, M. E., Pérez, J. J., Dwivedi, P., Zhou, M., McCarty, N. A., Stecenko, A. A., & Fernández, F. M. (2013). Ion mobility and liquid chromatography/mass spectrometry strategies for exhaled breath condensate glucose quantitation in cystic fibrosis studies. Rapid Communications in Mass Spectrometry, 27(20), 2263-2271. doi:10.1002/rcm.6683 es_ES
dc.description.references Sandín-España, P., Mateo-Miranda, M., López-Goti, C., De Cal, A., & Alonso-Prados, J. L. (2016). Development of a rapid and direct method for the determination of organic acids in peach fruit using LC–ESI-MS. Food Chemistry, 192, 268-273. doi:10.1016/j.foodchem.2015.07.012 es_ES
dc.description.references Bodachivskyi, I., Kuzhiumparambil, U., & Williams, D. B. G. (2018). Acid-Catalyzed Conversion of Carbohydrates into Value-Added Small Molecules in Aqueous Media and Ionic Liquids. ChemSusChem, 11(4), 642-660. doi:10.1002/cssc.201702016 es_ES
dc.description.references Csabai, P., & Joó, F. (2004). Synthesis and Catalytic Properties of New Water-Soluble Ruthenium(II)−N-Heterocyclic Carbene Complexes. Organometallics, 23(23), 5640-5643. doi:10.1021/om049511a es_ES
dc.description.references Bellarosa, L., Díez, J., Gimeno, J., Lledós, A., Suárez, F. J., Ujaque, G., & Vicent, C. (2012). Highly Efficient Redox Isomerisation of Allylic Alcohols Catalysed by Pyrazole-Based Ruthenium(IV) Complexes in Water: Mechanisms of Bifunctional Catalysis in Water. Chemistry - A European Journal, 18(25), 7749-7765. doi:10.1002/chem.201103374 es_ES
dc.description.references Schröder, D. (2012). Applications of Electrospray Ionization Mass Spectrometry in Mechanistic Studies and Catalysis Research. Accounts of Chemical Research, 45(9), 1521-1532. doi:10.1021/ar3000426 es_ES
dc.description.references Vikse, K. L., Ahmadi, Z., & Scott McIndoe, J. (2014). The application of electrospray ionization mass spectrometry to homogeneous catalysis. Coordination Chemistry Reviews, 279, 96-114. doi:10.1016/j.ccr.2014.06.012 es_ES
dc.description.references Yunker, L. P. E., Stoddard, R. L., & McIndoe, J. S. (2014). Practical approaches to the ESI-MS analysis of catalytic reactions. Journal of Mass Spectrometry, 49(1), 1-8. doi:10.1002/jms.3303 es_ES
dc.description.references Kawahara, R., Fujita, K., & Yamaguchi, R. (2012). Dehydrogenative Oxidation of Alcohols in Aqueous Media Using Water-Soluble and Reusable Cp*Ir Catalysts Bearing a Functional Bipyridine Ligand. Journal of the American Chemical Society, 134(8), 3643-3646. doi:10.1021/ja210857z es_ES
dc.description.references Trincado, M., Banerjee, D., & Grützmacher, H. (2014). Molecular catalysts for hydrogen production from alcohols. Energy Environ. Sci., 7(8), 2464-2503. doi:10.1039/c4ee00389f es_ES
dc.description.references Li, H., & Hall, M. B. (2013). Mechanism of the Formation of Carboxylate from Alcohols and Water Catalyzed by a Bipyridine-Based Ruthenium Complex: A Computational Study. Journal of the American Chemical Society, 136(1), 383-395. doi:10.1021/ja410541v es_ES
dc.description.references Rodríguez-Lugo, R. E., Trincado, M., Vogt, M., Tewes, F., Santiso-Quinones, G., & Grützmacher, H. (2013). A homogeneous transition metal complex for clean hydrogen production from methanol–water mixtures. Nature Chemistry, 5(4), 342-347. doi:10.1038/nchem.1595 es_ES
dc.description.references Vicent, C., & Gusev, D. G. (2016). ESI-MS Insights into Acceptorless Dehydrogenative Coupling of Alcohols. ACS Catalysis, 6(5), 3301-3309. doi:10.1021/acscatal.6b00623 es_ES
dc.description.references Spasyuk, D., Vicent, C., & Gusev, D. G. (2015). Chemoselective Hydrogenation of Carbonyl Compounds and Acceptorless Dehydrogenative Coupling of Alcohols. Journal of the American Chemical Society, 137(11), 3743-3746. doi:10.1021/ja512389y es_ES


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