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Highly active hybrid mesoporous silica-supported base organocatalysts for C-C bond formation

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Highly active hybrid mesoporous silica-supported base organocatalysts for C-C bond formation

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dc.contributor.author Erigoni, Andrea es_ES
dc.contributor.author Hernández Soto, María Consuelo es_ES
dc.contributor.author Rey Garcia, Fernando es_ES
dc.contributor.author Segarra-Almela, Mª De La Candelaria es_ES
dc.contributor.author DÍAZ MORALES, URBANO MANUEL es_ES
dc.date.accessioned 2021-04-17T03:32:18Z
dc.date.available 2021-04-17T03:32:18Z
dc.date.issued 2020-04-01 es_ES
dc.identifier.issn 0920-5861 es_ES
dc.identifier.uri http://hdl.handle.net/10251/165275
dc.description.abstract [EN] New base hybrid catalysts, based on silyl-derivatives of molecules carrying amino, diamino, pyrrolidine, pyrazolium and imidazolium functionalities have been successfully achieved through post synthetic grafting onto M41S-type support. Different characterization techniques were implemented to study the characteristics of the materials, such as elemental analysis, solid state MAS NMR and FTIR spectroscopies, X-ray diffraction (XRD), thermogravimetric and differential thermal analyses (TGA-DTA) and textural properties through N-2 physisorption analysis. The catalytic activity and recyclability of these compounds as base catalysts was demonstrated for C-C bond forming reactions such as Knoevenagel condensations and Michael additions rationalizing the differences observed as function of the reaction mechanisms. An enamine mechanism was proposed for Knoevenagel condensations and an enolate mechanism for Michael additions. es_ES
dc.description.sponsorship The authors are grateful for financial support from the Spanish Government by MAT2017-82288-C2-1-P and Severo Ochoa Excellence ProgramSEV-2016-0683. The authors thank the MULTY2HYCAT (EUHorizon 2020 funded project under grant agreement no. 720783). A. E. acknowledges "La Caixa" foundation for PhD scholarship. es_ES
dc.language Inglés es_ES
dc.publisher Elsevier es_ES
dc.relation.ispartof Catalysis Today es_ES
dc.rights Reconocimiento - No comercial - Sin obra derivada (by-nc-nd) es_ES
dc.subject Organic-inorganic hybrid catalysts es_ES
dc.subject Base sites es_ES
dc.subject Mesoporous and microporous materials es_ES
dc.subject C-C bond forming reactions es_ES
dc.title Highly active hybrid mesoporous silica-supported base organocatalysts for C-C bond formation es_ES
dc.type Artículo es_ES
dc.type Comunicación en congreso es_ES
dc.identifier.doi 10.1016/j.cattod.2019.09.041 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/H2020/720783/EU/MULTI-site organic-inorganic HYbrid CATalysts for MULTI-step chemical processes/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//SEV-2016-0683/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2017-82288-C2-1-P/ES/MATERIALES HIBRIDOS MULTIFUNCIONALES BASADOS EN NANO-UNIDADES ESTRUCTURALES ACTIVAS/ es_ES
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.description.bibliographicCitation Erigoni, A.; Hernández Soto, MC.; Rey Garcia, F.; Segarra-Almela, MDLC.; Díaz Morales, UM. (2020). Highly active hybrid mesoporous silica-supported base organocatalysts for C-C bond formation. Catalysis Today. 345:227-236. https://doi.org/10.1016/j.cattod.2019.09.041 es_ES
dc.description.accrualMethod S es_ES
dc.relation.conferencename 8th Czech-Italian-Spanish Conference on Molecular Sieves and Catalysis (CIS8) es_ES
dc.relation.conferencedate Junio 11-14,2019 es_ES
dc.relation.conferenceplace Amantea, Italy es_ES
dc.relation.publisherversion https://doi.org/10.1016/j.cattod.2019.09.041 es_ES
dc.description.upvformatpinicio 227 es_ES
dc.description.upvformatpfin 236 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 345 es_ES
dc.relation.pasarela S\406710 es_ES
dc.contributor.funder European Commission es_ES
dc.contributor.funder Fundació Bancària Caixa d'Estalvis i Pensions de Barcelona es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.description.references Díaz, U., Brunel, D., & Corma, A. (2013). Catalysis using multifunctional organosiliceous hybrid materials. Chemical Society Reviews, 42(9), 4083. doi:10.1039/c2cs35385g es_ES
dc.description.references Férey, G. (2008). Hybrid porous solids: past, present, future. Chem. Soc. Rev., 37(1), 191-214. doi:10.1039/b618320b es_ES
dc.description.references Loy, D. A., & Shea, K. J. (1995). Bridged Polysilsesquioxanes. Highly Porous Hybrid Organic-Inorganic Materials. Chemical Reviews, 95(5), 1431-1442. doi:10.1021/cr00037a013 es_ES
dc.description.references Hoffmann, F., Cornelius, M., Morell, J., & Fröba, M. (2006). Silica-Based Mesoporous Organic–Inorganic Hybrid Materials. Angewandte Chemie International Edition, 45(20), 3216-3251. doi:10.1002/anie.200503075 es_ES
dc.description.references Wight, A. P., & Davis, M. E. (2002). Design and Preparation of Organic−Inorganic Hybrid Catalysts. Chemical Reviews, 102(10), 3589-3614. doi:10.1021/cr010334m es_ES
dc.description.references Vallé, K., Belleville, P., Pereira, F., & Sanchez, C. (2006). Hierarchically structured transparent hybrid membranes by in situ growth of mesostructured organosilica in host polymer. Nature Materials, 5(2), 107-111. doi:10.1038/nmat1570 es_ES
dc.description.references Boury, B., & Corriu, R. J. P. (2002). Auto-organisation of hybrid organic–inorganic materials prepared by sol–gel chemistry. Chemical Communications, (8), 795-802. doi:10.1039/b109040m es_ES
dc.description.references Mehdi, A., Reye, C., & Corriu, R. (2011). From molecular chemistry to hybrid nanomaterials. Design and functionalization. Chem. Soc. Rev., 40(2), 563-574. doi:10.1039/b920516k es_ES
dc.description.references Sanchez, C., Julián, B., Belleville, P., & Popall, M. (2005). Applications of hybrid organic–inorganic nanocomposites. Journal of Materials Chemistry, 15(35-36), 3559. doi:10.1039/b509097k es_ES
dc.description.references Sanchez, C., Rozes, L., Ribot, F., Laberty-Robert, C., Grosso, D., Sassoye, C., … Nicole, L. (2010). «Chimie douce»: A land of opportunities for the designed construction of functional inorganic and hybrid organic-inorganic nanomaterials. Comptes Rendus Chimie, 13(1-2), 3-39. doi:10.1016/j.crci.2009.06.001 es_ES
dc.description.references Park, J.-W., Park, Y. J., & Jun, C.-H. (2011). Post-grafting of silica surfaces with pre-functionalized organosilanes: new synthetic equivalents of conventional trialkoxysilanes. Chemical Communications, 47(17), 4860. doi:10.1039/c1cc00038a es_ES
dc.description.references Lauwaert, J., De Canck, E., Esquivel, D., Thybaut, J. W., Van Der Voort, P., & Marin, G. B. (2013). Silanol-Assisted Aldol Condensation on Aminated Silica: Understanding the Arrangement of Functional Groups. ChemCatChem, 6(1), 255-264. doi:10.1002/cctc.201300742 es_ES
dc.description.references Yuan, H., Yoo, W.-J., Miyamura, H., & Kobayashi, S. (2012). Discovery of a Metalloenzyme-like Cooperative Catalytic System of Metal Nanoclusters and Catechol Derivatives for the Aerobic Oxidation of Amines. Journal of the American Chemical Society, 134(34), 13970-13973. doi:10.1021/ja306934b es_ES
dc.description.references McKittrick, M. W., & Jones, C. W. (2003). Toward Single-Site Functional MaterialsPreparation of Amine-Functionalized Surfaces Exhibiting Site-Isolated Behavior. Chemistry of Materials, 15(5), 1132-1139. doi:10.1021/cm020952z es_ES
dc.description.references McKittrick, M. W., & Jones, C. W. (2004). Toward Single-Site, Immobilized Molecular Catalysts:  Site-Isolated Ti Ethylene Polymerization Catalysts Supported on Porous Silica. Journal of the American Chemical Society, 126(10), 3052-3053. doi:10.1021/ja031725g es_ES
dc.description.references Zeidan, R. K., Hwang, S.-J., & Davis, M. E. (2006). Multifunctional Heterogeneous Catalysts: SBA-15-Containing Primary Amines and Sulfonic Acids. Angewandte Chemie International Edition, 45(38), 6332-6335. doi:10.1002/anie.200602243 es_ES
dc.description.references Brunelli, N. A., Venkatasubbaiah, K., & Jones, C. W. (2012). Cooperative Catalysis with Acid–Base Bifunctional Mesoporous Silica: Impact of Grafting and Co-condensation Synthesis Methods on Material Structure and Catalytic Properties. Chemistry of Materials, 24(13), 2433-2442. doi:10.1021/cm300753z es_ES
dc.description.references Lauwaert, J., Moschetta, E. G., Van Der Voort, P., Thybaut, J. W., Jones, C. W., & Marin, G. B. (2015). Spatial arrangement and acid strength effects on acid–base cooperatively catalyzed aldol condensation on aminosilica materials. Journal of Catalysis, 325, 19-25. doi:10.1016/j.jcat.2015.02.011 es_ES
dc.description.references Bass, J. D., Solovyov, A., Pascall, A. J., & Katz, A. (2006). Acid−Base Bifunctional and Dielectric Outer-Sphere Effects in Heterogeneous Catalysis:  A Comparative Investigation of Model Primary Amine Catalysts. Journal of the American Chemical Society, 128(11), 3737-3747. doi:10.1021/ja057395c es_ES
dc.description.references Sharma, K. K., Buckley, R. P., & Asefa, T. (2008). Optimizing Acid−Base Bifunctional Mesoporous Catalysts for the Henry Reaction: Effects of the Surface Density and Site Isolation of Functional Groups. Langmuir, 24(24), 14306-14320. doi:10.1021/la8030107 es_ES
dc.description.references Collier, V. E., Ellebracht, N. C., Lindy, G. I., Moschetta, E. G., & Jones, C. W. (2015). Kinetic and Mechanistic Examination of Acid–Base Bifunctional Aminosilica Catalysts in Aldol and Nitroaldol Condensations. ACS Catalysis, 6(1), 460-468. doi:10.1021/acscatal.5b02398 es_ES
dc.description.references Ma, T.-Y., Li, H., Deng, Q.-F., Liu, L., Ren, T.-Z., & Yuan, Z.-Y. (2012). Ordered Mesoporous Metal–Organic Frameworks Consisting of Metal Disulfonates. Chemistry of Materials, 24(12), 2253-2255. doi:10.1021/cm301256r es_ES
dc.description.references Kim, K. C., Moschetta, E. G., Jones, C. W., & Jang, S. S. (2016). Molecular Dynamics Simulations of Aldol Condensation Catalyzed by Alkylamine-Functionalized Crystalline Silica Surfaces. Journal of the American Chemical Society, 138(24), 7664-7672. doi:10.1021/jacs.6b03309 es_ES
dc.description.references Brunelli, N. A., & Jones, C. W. (2013). Tuning acid–base cooperativity to create next generation silica-supported organocatalysts. Journal of Catalysis, 308, 60-72. doi:10.1016/j.jcat.2013.05.022 es_ES
dc.description.references Brunelli, N. A., Didas, S. A., Venkatasubbaiah, K., & Jones, C. W. (2012). Tuning Cooperativity by Controlling the Linker Length of Silica-Supported Amines in Catalysis and CO2 Capture. Journal of the American Chemical Society, 134(34), 13950-13953. doi:10.1021/ja305601g es_ES
dc.description.references De Vylder, A., Lauwaert, J., Esquivel, D., Poelman, D., De Clercq, J., Van Der Voort, P., & Thybaut, J. W. (2018). The role of water in the reusability of aminated silica catalysts for aldol reactions. Journal of Catalysis, 361, 51-61. doi:10.1016/j.jcat.2018.02.016 es_ES
dc.description.references Sing, K. S. W. (1985). Reporting physisorption data for gas/solid systems with special reference to the determination of surface area and porosity (Recommendations 1984). Pure and Applied Chemistry, 57(4), 603-619. doi:10.1351/pac198557040603 es_ES
dc.description.references Barrett, E. P., Joyner, L. G., & Halenda, P. P. (1951). The Determination of Pore Volume and Area Distributions in Porous Substances. I. Computations from Nitrogen Isotherms. Journal of the American Chemical Society, 73(1), 373-380. doi:10.1021/ja01145a126 es_ES
dc.description.references Mokaya, R., & Jones, W. (1998). The influence of template extraction on the properties of primary amine templated aluminosilicate mesoporous molecular sieves. Journal of Materials Chemistry, 8(12), 2819-2826. doi:10.1039/a806049e es_ES
dc.description.references Tanev, P. T., & Pinnavaia, T. J. (1995). A Neutral Templating Route to Mesoporous Molecular Sieves. Science, 267(5199), 865-867. doi:10.1126/science.267.5199.865 es_ES
dc.description.references Kawahara, K., Hagiwara, Y., Shimojima, A., & Kuroda, K. (2008). Stepwise silylation of double-four-ring (D4R) silicate into a novel spherical siloxane with a defined architecture. Journal of Materials Chemistry, 18(27), 3193. doi:10.1039/b807533f es_ES
dc.description.references Haddad, B., Mokhtar, D., Goussem, M., Belarbi, E., Villemin, D., Bresson, S., … Kiefer, J. (2017). Influence of methyl and propyl groups on the vibrational spectra of two imidazolium ionic liquids and their non-ionic precursors. Journal of Molecular Structure, 1134, 582-590. doi:10.1016/j.molstruc.2017.01.008 es_ES
dc.description.references Rodriguez, I., Iborra, S., Corma, A., Rey, F., & Jordá, J. L. (1999). MCM-41–Quaternary organic tetraalkylammonium hydroxide composites as strong and stable Brønsted base catalysts. Chemical Communications, (7), 593-594. doi:10.1039/a900384c es_ES
dc.description.references CLIMENT, M. (2004). Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures. Journal of Catalysis, 225(2), 316-326. doi:10.1016/j.jcat.2004.04.027 es_ES
dc.description.references Prout, F. S., Beaucaire, V. D., Dyrkacz, G. R., Koppes, W. M., Kuznicki, R. E., Marlewski, T. A., … Puda, J. M. (1973). Konevenagel Reaction. Kinetic study of the reaction of (+)-3-methyl-cyclohexanone with malononitrile. The Journal of Organic Chemistry, 38(8), 1512-1517. doi:10.1021/jo00948a015 es_ES
dc.description.references Guyot, J., & Kergomard, A. (1983). Cinétique et mécanisme de la réaction de knoevenagel dans le benzène-2. Tetrahedron, 39(7), 1167-1179. doi:10.1016/s0040-4020(01)91880-0 es_ES
dc.description.references Lubisch, W., Beckenbach, E., Bopp, S., Hofmann, H.-P., Kartal, A., Kästel, C., … Möller, A. (2003). Benzoylalanine-Derived Ketoamides Carrying Vinylbenzyl Amino Residues:  Discovery of Potent Water-Soluble Calpain Inhibitors with Oral Bioavailability. Journal of Medicinal Chemistry, 46(12), 2404-2412. doi:10.1021/jm0210717 es_ES
dc.description.references Vlok, N., Malan, S. F., Castagnoli, N., Bergh, J. J., & Petzer, J. P. (2006). Inhibition of monoamine oxidase B by analogues of the adenosine A2A receptor antagonist (E)-8-(3-chlorostyryl)caffeine (CSC). Bioorganic & Medicinal Chemistry, 14(10), 3512-3521. doi:10.1016/j.bmc.2006.01.011 es_ES
dc.description.references Selvam, C., Jachak, S. M., Thilagavathi, R., & Chakraborti, A. K. (2005). Design, synthesis, biological evaluation and molecular docking of curcumin analogues as antioxidant, cyclooxygenase inhibitory and anti-inflammatory agents. Bioorganic & Medicinal Chemistry Letters, 15(7), 1793-1797. doi:10.1016/j.bmcl.2005.02.039 es_ES
dc.description.references Nakayama, K., Ishida, Y., Ohtsuka, M., Kawato, H., Yoshida, K., Yokomizo, Y., … Watkins, W. J. (2003). MexAB-OprM-Specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 1: Discovery and early strategies for lead optimization. Bioorganic & Medicinal Chemistry Letters, 13(23), 4201-4204. doi:10.1016/j.bmcl.2003.07.024 es_ES
dc.description.references Inagaki, S., Guan, S., Ohsuna, T., & Terasaki, O. (2002). An ordered mesoporous organosilica hybrid material with a crystal-like wall structure. Nature, 416(6878), 304-307. doi:10.1038/416304a es_ES
dc.description.references Jung, J., Jo, C., Cho, K., & Ryoo, R. (2012). Zeolite nanosheet of a single-pore thickness generated by a zeolite-structure-directing surfactant. Journal of Materials Chemistry, 22(11), 4637. doi:10.1039/c2jm16539b es_ES
dc.description.references Bellussi, G., Montanari, E., Di Paola, E., Millini, R., Carati, A., Rizzo, C., … Zanardi, S. (2011). ECS-3: A Crystalline Hybrid Organic-Inorganic Aluminosilicate with Open Porosity. Angewandte Chemie International Edition, 51(3), 666-669. doi:10.1002/anie.201105496 es_ES
dc.description.references Gaona, A., Moreno, J. M., Velty, A., Díaz, U., & Corma, A. (2014). One-pot synthesis of hierarchical porous layered hybrid materials based on aluminosilicate sheets and organic functional pillars. J. Mater. Chem. A, 2(45), 19360-19375. doi:10.1039/c4ta04742g es_ES
dc.description.references Knoevenagel, E. (1898). Condensation von Malonsäure mit aromatischen Aldehyden durch Ammoniak und Amine. Berichte der deutschen chemischen Gesellschaft, 31(3), 2596-2619. doi:10.1002/cber.18980310308 es_ES
dc.description.references Rodriguez, I., Iborra, S., Rey, F., & Corma, A. (2000). Heterogeneized Brönsted base catalysts for fine chemicals production: grafted quaternary organic ammonium hydroxides as catalyst for the production of chromenes and coumarins. Applied Catalysis A: General, 194-195, 241-252. doi:10.1016/s0926-860x(99)00371-3 es_ES


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