Selective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and decorated platinum nanoparticle

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dc.contributor.affiliationInstituto Universitario Mixto de Tecnología Química
dc.contributor.authorCisneros Reyes, Larisha Yaniraes_ES
dc.contributor.authorSerna Merino, Pedro Manuel
dc.contributor.authorCorma Canós, Avelino
dc.contributor.funderMinisterio de Economía y Competitividades_ES
dc.contributor.funderConsejo Nacional de Ciencia y Tecnología, México
dc.contributor.funderGeneralitat Valenciana
dc.date.accessioned2016-01-18T09:28:29Z
dc.date.issued2014-08-25
dc.description.abstractNitrones were synthesized in high yields directly from nitro compounds, aldehydes, and H-2 using carbon-decorated platinum nanoparticles. The high selectivity for nitrone synthesis contrasts that of common supported metal catalysts and corresponds to an increase from roughly 6 to 97%. The catalytic performance is tuned by precise control of the structure of the active sites and the characteristics of the support.es_ES
dc.description.accrualMethodSes_ES
dc.description.bibliographicCitationCisneros Reyes, LY.; Serna Merino, PM.; Corma Canós, A. (2014). Selective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and decorated platinum nanoparticle. Angewandte Chemie International Edition. 53(35):9306-9310. https://doi.org/10.1002/anie.201402878es_ES
dc.description.issue35es_ES
dc.description.referencesScott, G., & Smith, K. V. (1978). Mechanisms of antioxidant action: Auto-synergistic behaviour of nitrones. European Polymer Journal, 14(1), 39-43. doi:10.1016/0014-3057(78)90149-0es_ES
dc.description.referencesLee, K. J., & Kim, D. H. (1998). Inhibition of thermolysin with nitrone-bearing substrate analogs: A new type of thermolysin inhibitors. Bioorganic & Medicinal Chemistry Letters, 8(4), 323-326. doi:10.1016/s0960-894x(98)00023-7es_ES
dc.description.referencesGothelf, K. V., & Jørgensen, K. A. (1998). Asymmetric 1,3-Dipolar Cycloaddition Reactions. Chemical Reviews, 98(2), 863-910. doi:10.1021/cr970324ees_ES
dc.description.referencesMarco-Contelles, J. (2004). β-Lactam Synthesis by the Kinugasa Reaction. Angewandte Chemie International Edition, 43(17), 2198-2200. doi:10.1002/anie.200301730es_ES
dc.description.referencesMarco-Contelles, J. (2004). β-Lactam-Synthese durch die Kinugasa-Reaktion. Angewandte Chemie, 116(17), 2248-2250. doi:10.1002/ange.200301730es_ES
dc.description.referencesMasson, G., Cividino, P., Py, S., & Vallée, Y. (2003). SmI2-Induced Umpolung of the CN Bond: First Reductive Conjugate Addition of Nitrones to α,β-Unsaturated Esters. Angewandte Chemie International Edition, 42(20), 2265-2268. doi:10.1002/anie.200250480es_ES
dc.description.referencesMasson, G., Cividino, P., Py, S., & Vallée, Y. (2003). Angewandte Chemie, 115(20), 2367-2370. doi:10.1002/ange.200250480es_ES
dc.description.referencesEvans, D. A., Song, H.-J., & Fandrick, K. R. (2006). Enantioselective Nitrone Cycloadditions of α,β-Unsaturated 2-Acyl Imidazoles Catalyzed by Bis(oxazolinyl)pyridine−Cerium(IV) Triflate Complexes. Organic Letters, 8(15), 3351-3354. doi:10.1021/ol061223ies_ES
dc.description.referencesCarmona, D., Lamata, M. P., Viguri, F., Rodríguez, R., Oro, L. A., Lahoz, F. J., … Merino, P. (2005). Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to Methacrolein Catalyzed by (η5-C5Me5)M{(R)-Prophos} Containing Complexes (M = Rh, Ir; (R)-Prophos = 1,2-bis(Diphenylphosphino)propane):  On the Origin of the Enantioselectivity. Journal of the American Chemical Society, 127(38), 13386-13398. doi:10.1021/ja0539443es_ES
dc.description.referencesGawade, S. A., Bhunia, S., & Liu, R.-S. (2012). Intermolecular Gold-Catalyzed Diastereo- and Enantioselective [2+2+3] Cycloadditions of 1,6-Enynes with Nitrones. Angewandte Chemie International Edition, 51(31), 7835-7838. doi:10.1002/anie.201203507es_ES
dc.description.referencesGawade, S. A., Bhunia, S., & Liu, R.-S. (2012). Intermolecular Gold-Catalyzed Diastereo- and Enantioselective [2+2+3] Cycloadditions of 1,6-Enynes with Nitrones. Angewandte Chemie, 124(31), 7955-7958. doi:10.1002/ange.201203507es_ES
dc.description.referencesYoung, I. S., & Kerr, M. A. (2003). A Homo [3+2] Dipolar Cycloaddition: The Reaction of Nitrones with Cyclopropanes. Angewandte Chemie International Edition, 42(26), 3023-3026. doi:10.1002/anie.200351573es_ES
dc.description.referencesYoung, I. S., & Kerr, M. A. (2003). Angewandte Chemie, 115(26), 3131-3134. doi:10.1002/ange.200351573es_ES
dc.description.referencesQian, Y., Xu, X., Wang, X., Zavalij, P. J., Hu, W., & Doyle, M. P. (2012). Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways. Angewandte Chemie International Edition, 51(24), 5900-5903. doi:10.1002/anie.201202525es_ES
dc.description.referencesQian, Y., Xu, X., Wang, X., Zavalij, P. J., Hu, W., & Doyle, M. P. (2012). Rhodium(II)- and Copper(II)-Catalyzed Reactions of Enol Diazoacetates with Nitrones: Metal Carbene versus Lewis Acid Directed Pathways. Angewandte Chemie, 124(24), 6002-6005. doi:10.1002/ange.201202525es_ES
dc.description.referencesCardona, F., & Goti, A. (2005). The Discovery of Novel Metal-Induced Reactions of Nitrones: Not Only Electrophiles and Reagents for [3+2] Cycloadditions. Angewandte Chemie International Edition, 44(48), 7832-7835. doi:10.1002/anie.200502640es_ES
dc.description.referencesCardona, F., & Goti, A. (2005). Die Entdeckung neuer metallinduzierter Reaktionen von Nitronen: mehr als nur Elektrophile und Reagentien für [3+2]-Cycloadditionen. Angewandte Chemie, 117(48), 8042-8045. doi:10.1002/ange.200502640es_ES
dc.description.referencesLiu, F., Qian, D., Li, L., Zhao, X., & Zhang, J. (2010). Diastereo- and Enantioselective Gold(I)-Catalyzed Intermolecular Tandem Cyclization/[3+3]Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with Nitrones. Angewandte Chemie International Edition, 49(37), 6669-6672. doi:10.1002/anie.201003136es_ES
dc.description.referencesLiu, F., Qian, D., Li, L., Zhao, X., & Zhang, J. (2010). Diastereo- and Enantioselective Gold(I)-Catalyzed Intermolecular Tandem Cyclization/[3+3]Cycloadditions of 2-(1-Alkynyl)-2-alken-1-ones with Nitrones. Angewandte Chemie, 122(37), 6819-6822. doi:10.1002/ange.201003136es_ES
dc.description.referencesHamer, J., & Macaluso, A. (1964). Nitrones. Chemical Reviews, 64(4), 473-495. doi:10.1021/cr60230a006es_ES
dc.description.referencesMurray, R. W., & Singh, M. (1990). Chemistry of dioxiranes. 16. A facile one step synthesis of C-aryl nitrones using dimethyldioxirane. The Journal of Organic Chemistry, 55(9), 2954-2957. doi:10.1021/jo00296a073es_ES
dc.description.referencesMurahashi, S., Mitsui, H., Shiota, T., Tsuda, T., & Watanabe, S. (1990). Tungstate-catalyzed oxidation of secondary amines to nitrones. .alpha.-Substitution of secondary amines via nitrones. The Journal of Organic Chemistry, 55(6), 1736-1744. doi:10.1021/jo00293a013es_ES
dc.description.referencesCicchi, S., Goti, A., & Brandi, A. (1995). A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine. The Journal of Organic Chemistry, 60(15), 4743-4748. doi:10.1021/jo00120a016es_ES
dc.description.referencesChristensen, D., & Joergensen, K. A. (1989). Oxidation of imines to nitrones by the permanganate ion. The Journal of Organic Chemistry, 54(1), 126-131. doi:10.1021/jo00262a029es_ES
dc.description.referencesDondoni, A., Franco, S., Junquera, F., Merchán, F. L., Merino, P., & Tejero, T. (1994). Synthesis of N-Benzyl Nitrones. Synthetic Communications, 24(18), 2537-2550. doi:10.1080/00397919408010565es_ES
dc.description.referencesBuehler, E. (1967). Alkylation of syn- and anti-benzaldoximes. The Journal of Organic Chemistry, 32(2), 261-265. doi:10.1021/jo01288a002es_ES
dc.description.referencesBlaser, H.-U., Steiner, H., & Studer, M. (2009). Selective Catalytic Hydrogenation of Functionalized Nitroarenes: An Update. ChemCatChem, 1(2), 210-221. doi:10.1002/cctc.200900129es_ES
dc.description.referencesCorma, A., Serna, P., & García, H. (2007). Gold Catalysts Open a New General Chemoselective Route to Synthesize Oximes by Hydrogenation of α,β-Unsaturated Nitrocompounds with H2. Journal of the American Chemical Society, 129(20), 6358-6359. doi:10.1021/ja0704131es_ES
dc.description.referencesRubio-Marqués, P., Hernández-Garrido, J. C., Leyva-Pérez, A., & Corma, A. (2014). One pot synthesis of cyclohexanone oxime from nitrobenzene using a bifunctional catalyst. Chem. Commun., 50(14), 1645-1647. doi:10.1039/c3cc47693fes_ES
dc.description.referencesGautheron-Chapoulaud, V., Pandya, S. U., Cividino, P., Masson, G., Py, S., & Vallée, Y. (2001). One-Pot Synthesis of Functionalized Nitrones from Nitro Compounds. Synlett, 2001(08), 1281-1283. doi:10.1055/s-2001-16042es_ES
dc.description.referencesNigra, M. M., Arslan, I., & Katz, A. (2012). Gold nanoparticle-catalyzed reduction in a model system: Quantitative determination of reactive heterogeneity of a supported nanoparticle surface. Journal of Catalysis, 295, 115-121. doi:10.1016/j.jcat.2012.08.001es_ES
dc.description.referencesCorma, A., Serna, P., Concepción, P., & Calvino, J. J. (2008). Transforming Nonselective into Chemoselective Metal Catalysts for the Hydrogenation of Substituted Nitroaromatics. Journal of the American Chemical Society, 130(27), 8748-8753. doi:10.1021/ja800959ges_ES
dc.description.referencesCorma, A. (2006). Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts. Science, 313(5785), 332-334. doi:10.1126/science.1128383es_ES
dc.description.referencesSerna, P., Boronat, M., & Corma, A. (2011). Tuning the Behavior of Au and Pt Catalysts for the Chemoselective Hydrogenation of Nitroaromatic Compounds. Topics in Catalysis, 54(5-7), 439-446. doi:10.1007/s11244-011-9668-zes_ES
dc.description.referencesSantos, L. L., Serna, P., & Corma, A. (2009). Chemoselective Synthesis of Substituted Imines, Secondary Amines, and β-Amino Carbonyl Compounds from Nitroaromatics through Cascade Reactions on Gold Catalysts. Chemistry - A European Journal, 15(33), 8196-8203. doi:10.1002/chem.200900884es_ES
dc.description.referencesSerna, P., Concepción, P., & Corma, A. (2009). Design of highly active and chemoselective bimetallic gold–platinum hydrogenation catalysts through kinetic and isotopic studies. Journal of Catalysis, 265(1), 19-25. doi:10.1016/j.jcat.2009.04.004es_ES
dc.description.referencesTauster, S. J., Fung, S. C., & Garten, R. L. (1978). Strong metal-support interactions. Group 8 noble metals supported on titanium dioxide. Journal of the American Chemical Society, 100(1), 170-175. doi:10.1021/ja00469a029es_ES
dc.description.referencesCorma, A., Concepción, P., & Serna, P. (2007). A Different Reaction Pathway for the Reduction of Aromatic Nitro Compounds on Gold Catalysts. Angewandte Chemie International Edition, 46(38), 7266-7269. doi:10.1002/anie.200700823es_ES
dc.description.referencesCorma, A., Concepción, P., & Serna, P. (2007). A Different Reaction Pathway for the Reduction of Aromatic Nitro Compounds on Gold Catalysts. Angewandte Chemie, 119(38), 7404-7407. doi:10.1002/ange.200700823es_ES
dc.description.referencesBoronat, M., Concepción, P., Corma, A., González, S., Illas, F., & Serna, P. (2007). A Molecular Mechanism for the Chemoselective Hydrogenation of Substituted Nitroaromatics with Nanoparticles of Gold on TiO2Catalysts:  A Cooperative Effect between Gold and the Support. Journal of the American Chemical Society, 129(51), 16230-16237. doi:10.1021/ja076721ges_ES
dc.description.referencesSarkany, J., & D. Gonzalez, R. (1983). Support and dispersion effects on silica- and alumina-supported platinum catalysts. Applied Catalysis, 5(1), 85-97. doi:10.1016/0166-9834(83)80297-8es_ES
dc.description.referencesJin, T., Zhou, Y., Mains, G. J., & White, J. M. (1987). Infrared and x-ray photoelectron spectroscopy study of carbon monoxide and carbon dioxide on platinum/ceria. The Journal of Physical Chemistry, 91(23), 5931-5937. doi:10.1021/j100307a023es_ES
dc.description.referencesBoccuzzi, F., Chiorino, A., & Guglielminotti, E. (1996). Effects of structural defects and alloying on the FTIR spectra of CO adsorbed on. Surface Science, 368(1-3), 264-269. doi:10.1016/s0039-6028(96)01060-6es_ES
dc.description.sponsorshipThe research was supported by Project CONSOLIDER INGENIO (MULTICAT), PROMETEO, the SEVERO OCHOA Program for centers of excellence, the "Subprograma Ramon y Cajal" (contract RYC-2012-10662 to P.S.), and the CONACyT Program (fellowship to L.C.).en_EN
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dc.identifier.doi10.1002/anie.201402878
dc.identifier.eissn1521-3773
dc.identifier.issn1433-7851
dc.identifier.urihttps://riunet.upv.es/handle/10251/59968
dc.languageIngléses_ES
dc.publisherWiley-VCH Verlages_ES
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dc.relation.publisherversionhttp://dx.doi.org/10.1002/anie.201402878es_ES
dc.relation.references10.1016/0014-3057(78)90149-0es_ES
dc.relation.references10.1016/S0960-894X(98)00023-7es_ES
dc.relation.references10.1021/cr970324ees_ES
dc.relation.references10.1002/anie.200301730es_ES
dc.relation.references10.1002/ange.200301730es_ES
dc.relation.references10.1002/anie.200250480es_ES
dc.relation.references10.1002/ange.200250480es_ES
dc.relation.references10.1021/ol061223ies_ES
dc.relation.references10.1021/ja0539443es_ES
dc.relation.references10.1002/anie.201203507es_ES
dc.relation.references10.1002/ange.201203507es_ES
dc.relation.references10.1002/anie.200351573es_ES
dc.relation.references10.1002/ange.200351573es_ES
dc.relation.references10.1002/anie.201202525es_ES
dc.relation.references10.1002/ange.201202525es_ES
dc.relation.references10.1002/anie.200502640es_ES
dc.relation.references10.1002/ange.200502640es_ES
dc.relation.references10.1002/anie.201003136es_ES
dc.relation.references10.1002/ange.201003136es_ES
dc.relation.references10.1021/cr60230a006es_ES
dc.relation.references10.1021/jo00296a073es_ES
dc.relation.references10.1021/jo00293a013es_ES
dc.relation.references10.1021/jo00120a016es_ES
dc.relation.references10.1021/jo00262a029es_ES
dc.relation.references10.1080/00397919408010565es_ES
dc.relation.references10.1021/jo01288a002es_ES
dc.relation.references10.1002/cctc.200900129es_ES
dc.relation.references10.1021/ja0704131es_ES
dc.relation.references10.1039/C3CC47693Fes_ES
dc.relation.references10.1055/s-2001-16042es_ES
dc.relation.references10.1016/j.jcat.2012.08.001es_ES
dc.relation.references10.1021/ja800959ges_ES
dc.relation.references10.1126/science.1128383es_ES
dc.relation.references10.1007/s11244-011-9668-zes_ES
dc.relation.references10.1002/chem.200900884es_ES
dc.relation.references10.1016/j.jcat.2009.04.004es_ES
dc.relation.references10.1021/ja00469a029es_ES
dc.relation.references10.1002/anie.200700823es_ES
dc.relation.references10.1002/ange.200700823es_ES
dc.relation.references10.1021/ja076721ges_ES
dc.relation.references10.1016/0166-9834(83)80297-8es_ES
dc.relation.references10.1021/j100307a023es_ES
dc.relation.references10.1016/S0039-6028(96)01060-6es_ES
dc.relation.senia282681es_ES
dc.rightsReserva de todos los derechoses_ES
dc.rights.accessRightsCerradoes_ES
dc.subjectcascade reactionses_ES
dc.subjecthydrogenationes_ES
dc.subjectsupported catalystses_ES
dc.subjectnitroneses_ES
dc.subject.classificationQUIMICA ORGANICAes_ES
dc.titleSelective reductive coupling of nitro compounds with aldehydes to nitrones in H2 using carbon-supported and decorated platinum nanoparticlees_ES
dc.typeArtículoes_ES
dc.type.versioninfo:eu-repo/semantics/publishedVersiones_ES
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