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Strong Organic Bases as Building Blocks of Mesoporous Hybrid Catalysts for C-C Forming Bond Reactions
No full text[EN] 1,8-Bis(tetramethylguanidino)naphthalene (TMGN), a neutral organic base that combines the properties of guanidine and the properties of proton sponges, was used as a building block to produce organicinorganic silica-based mesoporous hybrids with strong basic properties. The TMGN-based mesoporous hybrids (TMGN/SiO2) were prepared by a solgel route working at a neutral pH and low temperatures, which avoided the use of SDAs. TMGN has been modified in order to have two terminal reactive silyl groups able to perform co-condensation with a conventional organosilane (TMOS) used as a silicon source. This synthesis has allowed us to directly introduce the unmodified, functionalized TMGN as part of the walls of the mesoporous silica by a one-pot synthesis. TMGN/SiO2 hybrid materials present excellent catalytic properties for CC bond forming reactions: Knoevenagel, Henry (nitroaldol), and ClaisenSchmidt condensations. The activity of the hybrid materials is higher than that of the counterpart homogeneous catalyst.The authors thank the Spanish Government by Consolider Ingenio 2010 MULTICAT (number CSD2009-00050) and MAT2011 (number 29020-C02-01) projects. E. G. is grateful for the financial support from the Marie Curie Fellowship (grant number FP7-PEO-PLE-2009-IEF).Gianotti, E.; Díaz Morales, UM.; Velty, A.; Corma Canós, A. (2012). Strong organic bases as building blocks of mesoporous hybrid catalysts for C-C forming bond reactions. European Journal of Inorganic Chemistry. 32:5175-5185. https://doi.org/10.1002/ejic.201200716S5175518532Wight, A. P., & Davis, M. E. (2002). Design and Preparation of Organic−Inorganic Hybrid Catalysts. Chemical Reviews, 102(10), 3589-3614. doi:10.1021/cr010334mBigi, F., Carloni, S., Maggi, R., Mazzacani, A., & Sartori, G. (2000). Nitroaldol condensation promoted by organic bases tethered to amorphous silica and MCM-41-type materials. 12th International Congress on Catalysis, Proceedings of the 12th ICC, 3501-3506. doi:10.1016/s0167-2991(00)80565-0Cheng, S., Wang, X., & Chen, S.-Y. (2009). Applications of Amine-functionalized Mesoporous Silica in Fine Chemical Synthesis. Topics in Catalysis, 52(6-7), 681-687. doi:10.1007/s11244-009-9216-2Rodriguez, 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/a900384cRodriguez, 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)00371-3Blanc, A. C., Valle, S., Renard, G., Brunel, D., Macquarrie, D. J., & Quinn, C. R. (2000). The preparation and use of novel immobilised guanidine catalysts in base-catalysed epoxidation and condensation reactions. Green Chemistry, 2(6), 283-288. doi:10.1039/b005929nGianotti, E., Diaz, U., Coluccia, S., & Corma, A. (2011). Hybrid organic–inorganic catalytic mesoporous materials with proton sponges as building blocks. Physical Chemistry Chemical Physics, 13(24), 11702. doi:10.1039/c1cp20588aAlder, R. W. (1989). Strain effects on amine basicities. Chemical Reviews, 89(5), 1215-1223. doi:10.1021/cr00095a015Staab, H. A., Saupe, T., & Krieger, C. (2006). 4,5-Bis(dimethylamino)fluoren, ein neuer „Protonenschwamm”︁. Angewandte Chemie, 95(9), 748-749. doi:10.1002/ange.19830950924Staab, H. A., Höne, M., & Krieger, C. (1988). Synthesis, structure and basicity of 1,9-bis(dimethylamino)-dibenzothiophene and 1,9-bis(dimethylamino)-dibenzoselenophene1,2). 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Insignificance of P−H···P Hydrogen Bonding: Structural Chemistry of Neutral and Protonated 1,8-Di(phosphinyl)naphthalene. Journal of the American Chemical Society, 126(48), 15833-15843. doi:10.1021/ja045460xOzeryanskii, V. A., Pozharskii, A. F., Bieńko, A. J., Sawka-Dobrowolska, W., & Sobczyk, L. (2005). [NHN]+Hydrogen Bonding in Protonated 1,8-Bis(dimethylamino)-2,7-dimethoxynaphthalene. X-ray Diffraction, Infrared, and Theoretical ab Initio and DFT Studies. The Journal of Physical Chemistry A, 109(8), 1637-1642. doi:10.1021/jp040618lRaab, V., Kipke, J., Gschwind, R. M., & Sundermeyer, J. (2002). 1,8-Bis(tetramethylguanidino)naphthalene (TMGN): A New, Superbasic and Kinetically Active «Proton Sponge». Chemistry - A European Journal, 8(7), 1682-1693. doi:10.1002/1521-3765(20020402)8:73.0.co;2-rKovačević, B., Maksić, Z. B., Vianello, R., & Primorac, M. (2002). Computer aided design of organic superbases: the role of intramolecular hydrogen bonding. New J. Chem., 26(10), 1329-1334. doi:10.1039/b204072g(s. f.). doi:10.1021/jo034906Kovačević, B., & Maksić, Z. B. (2002). The Proton Affinity of the Superbase 1,8-Bis(tetramethylguanidino)naphthalene (TMGN) and Some Related Compounds: A Theoretical Study. Chemistry - A European Journal, 8(7), 1694-1702. doi:10.1002/1521-3765(20020402)8:73.0.co;2-dPrzybylski, P., Gierczyk, B., Schroeder, G., Zundel, G., Brzezinski, B., & Bartl, F. (2007). Spectroscopic and PM5 semiempirical studies of the proton accepting properties of 1,8-bis(tetramethylguanidino)naphthalene. Journal of Molecular Structure, 844-845, 157-165. doi:10.1016/j.molstruc.2007.03.029Wüstefeld, H.-U., Kaska, W. C., Schüth, F., Stucky, G. D., Bu, X., & Krebs, B. (2001). Übergangsmetallkomplexe des Protonenschwammes 4,9-Dichlorchino[7,8-h]chinolin: ein stark gekrümmtes aromatisches System und extreme „Out-of-plane“-Position des Übergangsmetallzentrums. Angewandte Chemie, 113(17), 3280-3282. doi:10.1002/1521-3757(20010903)113:173.0.co;2-rWild, U., Hübner, O., Maronna, A., Enders, M., Kaifer, E., Wadepohl, H., & Himmel, H.-J. (2008). The First Metal Complexes of the Proton Sponge 1,8-Bis(N,N,N′,N′-tetramethylguanidino)naphthalene: Syntheses and Properties. European Journal of Inorganic Chemistry, 2008(28), 4440-4447. doi:10.1002/ejic.200800677Pope, E. J. A., & Mackenzie, J. D. (1986). Sol-gel processing of silica. Journal of Non-Crystalline Solids, 87(1-2), 185-198. doi:10.1016/s0022-3093(86)80078-3Winter, R., Chan, J.-B., Frattini, R., & Jonas, J. (1988). The effect of fluoride on the sol-gel process. Journal of Non-Crystalline Solids, 105(3), 214-222. doi:10.1016/0022-3093(88)90310-9Reale, E., Leyva, A., Corma, A., Martínez, C., García, H., & Rey, F. (2005). A fluoride-catalyzed sol–gel route to catalytically active non-ordered mesoporous silica materials in the absence of surfactants. Journal of Materials Chemistry, 15(17), 1742. doi:10.1039/b415066jDíaz, U., García, T., Velty, A., & Corma, A. (2009). Hybrid organic–inorganic catalytic porous materials synthesized at neutral pH in absence of structural directing agents. Journal of Materials Chemistry, 19(33), 5970. doi:10.1039/b906821jXia, Y., Yang, Z.-Y., Xia, P., Bastow, K. F., Nakanishi, Y., & Lee, K.-H. (2000). Antitumor agents. Part 202: Novel 2′-amino chalcones: design, synthesis and biological evaluation. Bioorganic & Medicinal Chemistry Letters, 10(8), 699-701. doi:10.1016/s0960-894x(00)00072-xHSIEH, H.-K., TSAO, L.-T., WANG, J.-P., & LIN, C.-N. (2000). Synthesis and Anti-inflammatory Effect of Chalcones. Journal of Pharmacy and Pharmacology, 52(2), 163-171. doi:10.1211/0022357001773814Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. ., & Pratap, R. (2004). Synthesis and antihyperglycemic activity of chalcone based aryloxypropanolamines. 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Catalytic Activity of Proton Sponge: Application to Knoevenagel Condensation Reactions. Journal of Catalysis, 183(1), 14-23. doi:10.1006/jcat.1998.2380Prout, 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/jo00948a015Guyot, J., & Kergomard, A. (1983). Cinétique et mécanisme de la réaction de knoevenagel dans le benzène—1. Tetrahedron, 39(7), 1161-1166. doi:10.1016/s0040-4020(01)91879-4Luzzio, F. A. (2001). The Henry reaction: recent examples. Tetrahedron, 57(6), 915-945. doi:10.1016/s0040-4020(00)00965-0Sartori, G. (2004). Catalytic activity of aminopropyl xerogels in the selective synthesis of (E)-nitrostyrenes from nitroalkanes and aromatic aldehydes. Journal of Catalysis, 222(2), 410-418. doi:10.1016/j.jcat.2003.11.016Climent, M. 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Efficient Bifunctional Nanocatalysts by Simple Postgrafting of Spatially Isolated Catalytic Groups on Mesoporous Materials. Angewandte Chemie, 119(16), 2937-2940. doi:10.1002/ange.200604570Xie, Y., Sharma, K. K., Anan, A., Wang, G., Biradar, A. V., & Asefa, T. (2009). Efficient solid-base catalysts for aldol reaction by optimizing the density and type of organoamine groups on nanoporous silica. Journal of Catalysis, 265(2), 131-140. doi:10.1016/j.jcat.2009.04.018Anan, A., Sharma, K. K., & Asefa, T. (2008). Selective, efficient nanoporous catalysts for nitroaldol condensation: Co-placement of multiple site-isolated functional groups on mesoporous materials. Journal of Molecular Catalysis A: Chemical, 288(1-2), 1-13. doi:10.1016/j.molcata.2008.03.027Wang, Q., & Shantz, D. F. (2010). Nitroaldol reactions catalyzed by amine-MCM-41 hybrids. Journal of Catalysis, 271(2), 170-177. doi:10.1016/j.jcat.2010.01.010Ballesteros, J. F., Sanz, M. J., Ubeda, A., Miranda, M. 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Hivernacles de CORMA (II), Premià de Dalt
No full textLa imatge ens mostra el cultiu de planta ornamental en els hivernacles de la cooperativa CORMA, distribuïdora i exportadora de la planta ornamental dels seus socis
Hivernacles de CORMA (IV), Premià de Dalt
No full textLa imatge ens mostra el cultiu de planta ornamental en els hivernacles de la cooperativa CORMA, distribuïdora i exportadora de la planta ornamental dels seus socis
Hybrid organic–inorganic catalytic mesoporous materials with proton sponges as building blocks
No full text[EN] Non-ordered organic-inorganic mesoporous hybrid materials with basic sites have been synthesized following a fluoride-catalysed sol-gel process at neutral pH and low temperatures that avoids the use of structural directing agents (SDAs). Proton sponges have been used as the organic builder of the hybrids, while the inorganic part corresponds to silica tetrahedra. The proton sponges are diamines that exhibit very high basicity and, after functionalization, have been introduced as part of the walls of the mesoporous silica by one-pot synthesis. Several hybrids with different organic loadings have been synthesized and characterized by gas adsorption, thermogravimetric and elemental analysis, solid state MAS-NMR and FTIR spectroscopy. These hybrids show high activity as base catalysts and can be recycled.The authors thank financial support by Consolider-Ingenio (MULTICAT project) from Spanish Government. EG thanks Marie Curie Fellowship (FP7-PEOPLE-2009-IEF) for financial support.Gianotti, E.; Díaz Morales, UM.; Coluccia, S.; Corma Canós, A. (2011). Hybrid organic-inorganic catalytic mesoporous materials with proton sponges as building blocks. Physical Chemistry Chemical Physics. 13(24):11702-11709. https://doi.org/10.1039/c1cp20588aS11702117091324Hoffmann, 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.200503075Sanchez, 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.2009.06.001Sanchez, C., Julián, B., Belleville, P., & Popall, M. (2005). Applications of hybrid organic–inorganic nanocomposites. 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Catalyst dispersion on supported ultramicroporous inorganic membranes using derivatized silylation agents. Applied Catalysis A: General, 96(1), 65-82. doi:10.1016/0926-860x(93)80007-dBoury, 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/b109040mMehdi, 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/b920516kPope, E. J. A., & Mackenzie, J. D. (1986). Sol-gel processing of silica. Journal of Non-Crystalline Solids, 87(1-2), 185-198. doi:10.1016/s0022-3093(86)80078-3Winter, R., Chan, J.-B., Frattini, R., & Jonas, J. (1988). The effect of fluoride on the sol-gel process. Journal of Non-Crystalline Solids, 105(3), 214-222. doi:10.1016/0022-3093(88)90310-9Reale, E., Leyva, A., Corma, A., Martínez, C., García, H., & Rey, F. (2005). A fluoride-catalyzed sol–gel route to catalytically active non-ordered mesoporous silica materials in the absence of surfactants. Journal of Materials Chemistry, 15(17), 1742. doi:10.1039/b415066jDíaz, U., García, T., Velty, A., & Corma, A. (2009). Hybrid organic–inorganic catalytic porous materials synthesized at neutral pH in absence of structural directing agents. Journal of Materials Chemistry, 19(33), 5970. doi:10.1039/b906821jAlder, R. W. (1989). Strain effects on amine basicities. Chemical Reviews, 89(5), 1215-1223. doi:10.1021/cr00095a015Llamas-Saiz, A. L., Foces-Foces, C., & Elguero, J. (1994). Proton sponges. Journal of Molecular Structure, 328, 297-323. doi:10.1016/0022-2860(94)08367-3Howard, S. T. (2000). Relationship between Basicity, Strain, and Intramolecular Hydrogen-Bond Energy in Proton Sponges. Journal of the American Chemical Society, 122(34), 8238-8244. doi:10.1021/ja0010094Rodriguez, I., Sastre, G., Corma, A., & Iborra, S. (1999). Catalytic Activity of Proton Sponge: Application to Knoevenagel Condensation Reactions. Journal of Catalysis, 183(1), 14-23. doi:10.1006/jcat.1998.2380CLIMENT, M., CORMA, A., DOMINGUEZ, I., IBORRA, S., SABATER, M., & SASTRE, G. (2007). Gem-diamines as highly active organocatalysts for carbon–carbon bond formation. Journal of Catalysis, 246(1), 136-146. doi:10.1016/j.jcat.2006.11.029Sing, 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/pac198557040603Barrett, 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/ja01145a126Woźniak, K. (1996). Proton sponges: solid-state NMR spectra of ionic complexes of 1,8-bis(dimethylamino)naphthalene. Journal of Molecular Structure, 374(1-3), 317-326. doi:10.1016/0022-2860(95)08947-0Pozharskii, A. F. (1998). Naphthalene «proton sponges». Russian Chemical Reviews, 67(1), 1-24. doi:10.1070/rc1998v067n01abeh000377Seo, Y.-K., Park, S.-B., & Ho Park, D. (2006). Mesoporous hybrid organosilica containing urethane moieties. Journal of Solid State Chemistry, 179(4), 1285-1288. doi:10.1016/j.jssc.2006.01.021Kawahara, 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/b807533fVan Meervelt, L., Platteborze, K., & Zeegers-Huyskens, T. (1994). X-Ray and Fourier-transform infrared studies of 1,8-bis(dimethylaminomethyl)naphthalene. Comparison with 1,8-bis(dimethylamino)naphthalene. Journal of the Chemical Society, Perkin Transactions 2, (5), 1087. doi:10.1039/p29940001087Brzeziński, B., Schroeder, G., Grech, E., Malarski, Z., & Sobczyk, L. (1992). Basicity, IR spectra and protonation of some proton sponges in acetonitrile. Journal of Molecular Structure, 274, 75-82. doi:10.1016/0022-2860(92)80147-aRodriguez, 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)00371-3CLIMENT, 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.2004.04.027Prout, 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/jo00948a015Guyot, J., & Kergomard, A. (1983). Cinétique et mécanisme de la réaction de knoevenagel dans le benzène—1. Tetrahedron, 39(7), 1161-1166. doi:10.1016/s0040-4020(01)91879-4Motokura, K., Tanaka, S., Tada, M., & Iwasawa, Y. (2009). Bifunctional Heterogeneous Catalysis of Silica-Alumina-Supported Tertiary Amines with Controlled Acid-Base Interactions for Efficient 1,4-Addition Reactions. Chemistry - A European Journal, 15(41), 10871-10879. doi:10.1002/chem.20090138
Cluster catalysis A Subtle form of recognition
No full textCorma Canós, A. (2014). Cluster catalysis A Subtle form of recognition. Nature Nanotechnology. 9(6):412-413. doi:10.1038/nnano.2014.114S41241396Haack, P. & Limberg, C. Angew. Chem. Int. Ed. 53, 4282–4293 (2014).Quintanar, L. et al. J. Am. Chem. Soc. 127, 13832–13845 (2005).Oliver-Meseguer, J., Cabrero-Antonino, J. R., Dominguez, I., Leyva-Perez, A. & Corma, A. Science 338, 1452–1455 (2012).Okrut, A. et al. Nature Nanotech. 9, 459–465 (2014).Tilekaratne, A., Simonovis, J. P., Lopez Fagundez, M. F., Ebrahimi, M. & Zaera, F. ACS Catal. 2, 2259–2268 (2012).Öfner, H. & Zaera, F. J. Am. Chem. Soc. 124, 10982–10983 (2002).Hwu, H. H., Eng, J. & Chen, J. G. J. Am. Chem. Soc. 124, 702–709 (2002).Boyer, J. L., Rochford, J., Tsai, M.-K., Muckerman, J. T. & Fujita, E. Coord. Chem. Rev. 254, 309–330 (2010)
CORMA-Passadissos per la venda, Premià de Dalt
No full textLa imatge ens mostra el cultiu de planta ornamental en els hivernacles de la cooperativa CORMA, distribuïdora i exportadora de la planta ornamental dels seus socis
Avelino Corma, investido Honoris Causa por la Universidad de Ottawa
No full textLugar: oTTAWA
Protagonistas: Avelino Corma
Tipo de evento: HonorisEn reconocimiento a sus importantes contribuciones en el campo de la catálisisZurano Conches, L. (2012). Avelino Corma, investido Honoris Causa por la Universidad de Ottawa. https://riunet.upv.es/handle/10251/16059
Planta ornamental en els hivernacles de CORMA, Premià de Dalt
No full textLa imatge ens mostra el cultiu de planta ornamental en els hivernacles de la cooperativa CORMA, distribuïdora i exportadora de la planta ornamental dels seus socis
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