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Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow

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Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow

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dc.contributor.author Rivero-Crespo, Miguel Ángel es_ES
dc.contributor.author Tejeda-Serrano, Maria es_ES
dc.contributor.author Perez-Sánchez, Horacio es_ES
dc.contributor.author Cerón-Carrasco, José Pedro es_ES
dc.contributor.author Leyva Perez, Antonio es_ES
dc.date.accessioned 2021-04-17T03:32:45Z
dc.date.available 2021-04-17T03:32:45Z
dc.date.issued 2020-03-02 es_ES
dc.identifier.issn 1433-7851 es_ES
dc.identifier.uri http://hdl.handle.net/10251/165285
dc.description This is the peer reviewed version of the following article: M. Á. Rivero-Crespo, M. Tejeda-Serrano, H. Pérez-Sánchez, J. P. Cerón-Carrasco, A. Leyva-Pérez, Angew. Chem. Int. Ed. 2020, 59, 3846, which has been published in final form at https://doi.org/10.1002/anie.201909597. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. es_ES
dc.description.abstract [EN] The carbonyl-olefin metathesis reaction has experienced significant advances in the last seven years with new catalysts and reaction protocols. However, most of these procedures involve soluble catalysts for intramolecular reactions in batch. Herein, we show that recoverable, inexpensive, easy to handle, non-toxic, and widely available simple solid acids, such as the aluminosilicate montmorillonite, can catalyze the intermolecular carbonyl-olefin metathesis of aromatic ketones and aldehydes with vinyl ethers in-flow, to give alkenes with complete trans stereoselectivity on multi-gram scale and high yields. Experimental and computational data support a mechanism based on a carbocation-induced Grob fragmentation. These results open the way for the industrial implementation of carbonyl-olefin metathesis over solid catalysts in continuous mode, which is still the origin and main application of the parent alkene-alkene cross-metathesis. es_ES
dc.description.sponsorship Financial support by MINECO through the Severo Ochoa program (SEV-2016-0683), Excellence program (CTQ 2017-86735-P, CTQ 2017-87974-R), Retos Col. (RTC-2017-6331-5), and "Convocatoria 2014 de Ayudas Fundacion BBVA a Investigadores y Creadores Culturales" is acknowledged. M.A.R.-C. and M.T.-S. thank ITQ for the concession of a contract. This research was partially supported by the supercomputing infrastructure of Poznan Supercomputing Center. es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation.ispartof Angewandte Chemie International Edition es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Carbonyl-olefin metathesis es_ES
dc.subject Heterogeneous catalysis es_ES
dc.subject In-flow reactions es_ES
dc.subject Montmorillonite K10 es_ES
dc.subject Vinyl ethers es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/anie.201909597 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-86735-P/ES/CATALISIS CON ATOMOS METALICOS AISLADOS Y CLUSTERES ULTRAPEQUEÑOS BIEN DEFINIDOS, SIN LIGANDOS Y CONFINADOS./ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI//RTC-2017-6331-5/ES/NUEVA SINTESIS DEL OLIGOMERO CLAVE EN TINTAS DIGITALES/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-87974-R/ES/DESARROLLO DE TECNICAS AVANZADAS DE DESCUBRIMIENTO DE FARMACOS, SU IMPLEMENTACION EN HERRAMIENTAS SOFTWARE Y WEB, Y SU APLICACION A CONTEXTOS DE RELEVANCIA FARMACOLOGICA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//SEV-2016-0683/ 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 Rivero-Crespo, MÁ.; Tejeda-Serrano, M.; Perez-Sánchez, H.; Cerón-Carrasco, JP.; Leyva Perez, A. (2020). Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow. Angewandte Chemie International Edition. 59(10):3846-3849. https://doi.org/10.1002/anie.201909597 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/anie.201909597 es_ES
dc.description.upvformatpinicio 3846 es_ES
dc.description.upvformatpfin 3849 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 59 es_ES
dc.description.issue 10 es_ES
dc.identifier.pmid 31538394 es_ES
dc.relation.pasarela S\404698 es_ES
dc.contributor.funder Fundación BBVA es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.description.references Becker, M. R., Watson, R. B., & Schindler, C. S. (2018). Beyond olefins: new metathesis directions for synthesis. Chemical Society Reviews, 47(21), 7867-7881. doi:10.1039/c8cs00391b es_ES
dc.description.references Griffith, A. K., Vanos, C. M., & Lambert, T. H. (2012). Organocatalytic Carbonyl-Olefin Metathesis. Journal of the American Chemical Society, 134(45), 18581-18584. doi:10.1021/ja309650u es_ES
dc.description.references Ludwig, J. R., Zimmerman, P. M., Gianino, J. B., & Schindler, C. S. (2016). Iron(III)-catalysed carbonyl–olefin metathesis. Nature, 533(7603), 374-379. doi:10.1038/nature17432 es_ES
dc.description.references Ludwig, J. R., Phan, S., McAtee, C. C., Zimmerman, P. M., Devery, J. J., & Schindler, C. S. (2017). Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction. Journal of the American Chemical Society, 139(31), 10832-10842. doi:10.1021/jacs.7b05641 es_ES
dc.description.references For reviews on carbonyl olefin metathesis see: es_ES
dc.description.references Schindler, C., & Ludwig, J. (2017). Lewis Acid Catalyzed Carbonyl–Olefin Metathesis. Synlett, 28(13), 1501-1509. doi:10.1055/s-0036-1588827 es_ES
dc.description.references T. H. Lambert Synlett2019 ahead of print. es_ES
dc.description.references For examples of solid-catalyzed low-temperature alkene metathesis see: es_ES
dc.description.references Mougel, V., Chan, K.-W., Siddiqi, G., Kawakita, K., Nagae, H., Tsurugi, H., … Copéret, C. (2016). Low Temperature Activation of Supported Metathesis Catalysts by Organosilicon Reducing Agents. ACS Central Science, 2(8), 569-576. doi:10.1021/acscentsci.6b00176 es_ES
dc.description.references Korzyński, M. D., Consoli, D. F., Zhang, S., Román-Leshkov, Y., & Dincă, M. (2018). Activation of Methyltrioxorhenium for Olefin Metathesis in a Zirconium-Based Metal–Organic Framework. Journal of the American Chemical Society, 140(22), 6956-6960. doi:10.1021/jacs.8b02837 es_ES
dc.description.references Van Schaik, H.-P., Vijn, R.-J., & Bickelhaupt, F. (1994). Acid-Catalyzed Olefination of Benzaldehyde. Angewandte Chemie International Edition in English, 33(1516), 1611-1612. doi:10.1002/anie.199416111 es_ES
dc.description.references Van Schaik, H.-P., Vijn, R.-J., & Bickelhaupt, F. (1994). Säurekatalysierte Olefinierung von Benzaldehyd. Angewandte Chemie, 106(15-16), 1703-1704. doi:10.1002/ange.19941061529 es_ES
dc.description.references For pure Bronsted acid-catalyzed reactions see: es_ES
dc.description.references Ludwig, J. R., Watson, R. B., Nasrallah, D. J., Gianino, J. B., Zimmerman, P. M., Wiscons, R. A., & Schindler, C. S. (2018). Interrupted carbonyl-olefin metathesis via oxygen atom transfer. Science, 361(6409), 1363-1369. doi:10.1126/science.aar8238 es_ES
dc.description.references Catti, L., & Tiefenbacher, K. (2018). Brønsted Acid-Catalyzed Carbonyl-Olefin Metathesis inside a Self-Assembled Supramolecular Host. Angewandte Chemie International Edition, 57(44), 14589-14592. doi:10.1002/anie.201712141 es_ES
dc.description.references Catti, L., & Tiefenbacher, K. (2018). Brønsted-Säure-katalysierte Carbonyl-Olefin-Metathese in einer selbstorganisierten supramolekularen Wirtstruktur. Angewandte Chemie, 130(44), 14797-14800. doi:10.1002/ange.201712141 es_ES
dc.description.references For intermolecular reactions see: es_ES
dc.description.references Ni, S., & Franzén, J. (2018). Carbocation catalysed ring closing aldehyde–olefin metathesis. Chemical Communications, 54(92), 12982-12985. doi:10.1039/c8cc06734a es_ES
dc.description.references Pitzer, L., Sandfort, F., Strieth‐Kalthoff, F., & Glorius, F. (2018). Carbonyl–Olefin Cross‐Metathesis Through a Visible‐Light‐Induced 1,3‐Diol Formation and Fragmentation Sequence. Angewandte Chemie International Edition, 57(49), 16219-16223. doi:10.1002/anie.201810221 es_ES
dc.description.references Pitzer, L., Sandfort, F., Strieth‐Kalthoff, F., & Glorius, F. (2018). Carbonyl‐Olefin‐Kreuzmetathese mittels Licht‐induzierter 1,3‐Diol‐Bildung‐ und Fragmentierungssequenz. Angewandte Chemie, 130(49), 16453-16457. doi:10.1002/ange.201810221 es_ES
dc.description.references Tran, U. P. N., Oss, G., Pace, D. P., Ho, J., & Nguyen, T. V. (2018). Tropylium-promoted carbonyl–olefin metathesis reactions. Chemical Science, 9(23), 5145-5151. doi:10.1039/c8sc00907d es_ES
dc.description.references Tran, U. P. N., Oss, G., Breugst, M., Detmar, E., Pace, D. P., Liyanto, K., & Nguyen, T. V. (2018). Carbonyl–Olefin Metathesis Catalyzed by Molecular Iodine. ACS Catalysis, 9(2), 912-919. doi:10.1021/acscatal.8b03769 es_ES
dc.description.references Lewis, J. D., Van de Vyver, S., & Román‐Leshkov, Y. (2015). Acid–Base Pairs in Lewis Acidic Zeolites Promote Direct Aldol Reactions by Soft Enolization. Angewandte Chemie International Edition, 54(34), 9835-9838. doi:10.1002/anie.201502939 es_ES
dc.description.references Lewis, J. D., Van de Vyver, S., & Román‐Leshkov, Y. (2015). Acid–Base Pairs in Lewis Acidic Zeolites Promote Direct Aldol Reactions by Soft Enolization. Angewandte Chemie, 127(34), 9973-9976. doi:10.1002/ange.201502939 es_ES
dc.description.references Fortea-Pérez, F. R., Mon, M., Ferrando-Soria, J., Boronat, M., Leyva-Pérez, A., Corma, A., … Pardo, E. (2017). The MOF-driven synthesis of supported palladium clusters with catalytic activity for carbene-mediated chemistry. Nature Materials, 16(7), 760-766. doi:10.1038/nmat4910 es_ES
dc.description.references Oliver-Meseguer, J., Boronat, M., Vidal-Moya, A., Concepción, P., Rivero-Crespo, M. Á., Leyva-Pérez, A., & Corma, A. (2018). Generation and Reactivity of Electron-Rich Carbenes on the Surface of Catalytic Gold Nanoparticles. Journal of the American Chemical Society, 140(9), 3215-3218. doi:10.1021/jacs.7b13696 es_ES
dc.description.references Rivero‐Crespo, M. A., Mon, M., Ferrando‐Soria, J., Lopes, C. W., Boronat, M., Leyva‐Pérez, A., … Pardo, E. (2018). Confined Pt 1 1+ Water Clusters in a MOF Catalyze the Low‐Temperature Water–Gas Shift Reaction with both CO 2 Oxygen Atoms Coming from Water. Angewandte Chemie International Edition, 57(52), 17094-17099. doi:10.1002/anie.201810251 es_ES
dc.description.references Rivero‐Crespo, M. A., Mon, M., Ferrando‐Soria, J., Lopes, C. W., Boronat, M., Leyva‐Pérez, A., … Pardo, E. (2018). Confined Pt 1 1+ Water Clusters in a MOF Catalyze the Low‐Temperature Water–Gas Shift Reaction with both CO 2 Oxygen Atoms Coming from Water. Angewandte Chemie, 130(52), 17340-17345. doi:10.1002/ange.201810251 es_ES
dc.description.references Tejeda-Serrano, M., Mon, M., Ross, B., Gonell, F., Ferrando-Soria, J., Corma, A., … Pardo, E. (2018). Isolated Fe(III)–O Sites Catalyze the Hydrogenation of Acetylene in Ethylene Flows under Front-End Industrial Conditions. Journal of the American Chemical Society, 140(28), 8827-8832. doi:10.1021/jacs.8b04669 es_ES
dc.description.references Ma, L., Li, W., Xi, H., Bai, X., Ma, E., Yan, X., & Li, Z. (2016). FeCl3 -Catalyzed Ring-Closing Carbonyl-Olefin Metathesis. Angewandte Chemie International Edition, 55(35), 10410-10413. doi:10.1002/anie.201604349 es_ES
dc.description.references Ma, L., Li, W., Xi, H., Bai, X., Ma, E., Yan, X., & Li, Z. (2016). FeCl3 -Catalyzed Ring-Closing Carbonyl-Olefin Metathesis. Angewandte Chemie, 128(35), 10566-10569. doi:10.1002/ange.201604349 es_ES
dc.description.references McAtee, C. C., Riehl, P. S., & Schindler, C. S. (2017). Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl–Olefin Metathesis. Journal of the American Chemical Society, 139(8), 2960-2963. doi:10.1021/jacs.7b01114 es_ES
dc.description.references Niyomchon, S., Oppedisano, A., Aillard, P., & Maulide, N. (2017). A three-membered ring approach to carbonyl olefination. Nature Communications, 8(1). doi:10.1038/s41467-017-01036-y es_ES
dc.description.references Watson, R. B., & Schindler, C. S. (2017). Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates. Organic Letters, 20(1), 68-71. doi:10.1021/acs.orglett.7b03367 es_ES
dc.description.references Groso, E. J., Golonka, A. N., Harding, R. A., Alexander, B. W., Sodano, T. M., & Schindler, C. S. (2018). 3-Aryl-2,5-Dihydropyrroles via Catalytic Carbonyl-Olefin Metathesis. ACS Catalysis, 8(3), 2006-2011. doi:10.1021/acscatal.7b03769 es_ES
dc.description.references Albright, H., Riehl, P. S., McAtee, C. C., Reid, J. P., Ludwig, J. R., Karp, L. A., … Schindler, C. S. (2018). Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) Homo-Dimers as Lewis Acidic Superelectrophiles. Journal of the American Chemical Society, 141(4), 1690-1700. doi:10.1021/jacs.8b11840 es_ES
dc.description.references Śliwa, M., Samson, K., Ruggiero–Mikołajczyk, M., Żelazny, A., & Grabowski, R. (2014). Influence of Montmorillonite K10 Modification with Tungstophosphoric Acid on Hybrid Catalyst Activity in Direct Dimethyl Ether Synthesis from Syngas. Catalysis Letters, 144(11), 1884-1893. doi:10.1007/s10562-014-1359-5 es_ES
dc.description.references Cabrero-Antonino, J. R., Leyva-Pérez, A., & Corma, A. (2015). Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis. Angewandte Chemie International Edition, 54(19), 5658-5661. doi:10.1002/anie.201500864 es_ES
dc.description.references Cabrero-Antonino, J. R., Leyva-Pérez, A., & Corma, A. (2015). Beyond Acid Strength in Zeolites: Soft Framework Counteranions for Stabilization of Carbocations on Zeolites and Its Implication in Organic Synthesis. Angewandte Chemie, 127(19), 5750-5753. doi:10.1002/ange.201500864 es_ES
dc.description.references Gassman, P. G., & Burns, S. J. (1988). General method for the synthesis of enol ethers (vinyl ethers) from acetals. The Journal of Organic Chemistry, 53(23), 5574-5576. doi:10.1021/jo00258a043 es_ES
dc.description.references Yamamoto, T., Eki, T., Nagumo, S., Suemune, H., & Sakai, K. (1992). Drastic ring transformation reactions of fused bicyclic rings to bridged bicyclic rings. Tetrahedron, 48(22), 4517-4524. doi:10.1016/s0040-4020(01)81224-2 es_ES
dc.description.references Nagumo, S., Matsukuma, A., Suemune, H., & Sakai, K. (1993). Novel ring cleavage based on intermolecular aldol condensation. Tetrahedron, 49(46), 10501-10510. doi:10.1016/s0040-4020(01)81545-3 es_ES
dc.description.references Suemune, H., Yoshida, O., Uchida, J., Nomura, Y., Tanaka, M., & Sakai, K. (1995). Asymmetric ring cleavage reaction based on crossed aldol condensation. Tetrahedron Letters, 36(40), 7259-7262. doi:10.1016/0040-4039(95)01504-b es_ES
dc.description.references Kumar, B. S., Dhakshinamoorthy, A., & Pitchumani, K. (2014). K10 montmorillonite clays as environmentally benign catalysts for organic reactions. Catal. Sci. Technol., 4(8), 2378-2396. doi:10.1039/c4cy00112e es_ES
dc.description.references Pérez-Ruiz, R., Miranda, M. A., Alle, R., Meerholz, K., & Griesbeck, A. G. (2006). An efficient carbonyl-alkene metathesis of bicyclic oxetanes: photoinduced electron transfer reduction of the Paternò–Büchi adducts from 2,3-dihydrofuran and aromatic aldehydes. Photochem. Photobiol. Sci., 5(1), 51-55. doi:10.1039/b513875b es_ES
dc.description.references D’Auria, M., & Racioppi, R. (2013). Oxetane Synthesis through the Paternò-Büchi Reaction. Molecules, 18(9), 11384-11428. doi:10.3390/molecules180911384 es_ES
dc.description.references Mete, T. B., Khopade, T. M., & Bhat, R. G. (2017). Oxidative decarboxylation of arylacetic acids in water: One-pot transition-metal-free synthesis of aldehydes and ketones. Tetrahedron Letters, 58(29), 2822-2825. doi:10.1016/j.tetlet.2017.06.013 es_ES
dc.description.references Corma, A., Ruiz, V. R., Leyva-Pérez, A., & Sabater, M. J. (2010). Regio- and Stereoselective Intermolecular Hydroalkoxylation of Alkynes Catalysed by Cationic Gold(I) Complexes. Advanced Synthesis & Catalysis, 352(10), 1701-1710. doi:10.1002/adsc.201000094 es_ES
dc.description.references Prantz, K., & Mulzer, J. (2010). Synthetic Applications of the Carbonyl Generating Grob Fragmentation. Chemical Reviews, 110(6), 3741-3766. doi:10.1021/cr900386h es_ES
dc.description.references Gong, Y. D., Tanaka, H., Iwasawa, N., & Narasaka, K. (1998). Lewis Acid-Promoted Disproportionation Reaction of Aromatic Vinyl Ethers and Acetals and Its Application to the Synthesis of Paracotoin. Bulletin of the Chemical Society of Japan, 71(9), 2181-2185. doi:10.1246/bcsj.71.2181 es_ES
dc.description.references Zhao, Y., & Truhlar, D. G. (2008). Density Functionals with Broad Applicability in Chemistry. Accounts of Chemical Research, 41(2), 157-167. doi:10.1021/ar700111a es_ES
dc.description.references Copéret, C., Allouche, F., Chan, K. W., Conley, M. P., Delley, M. F., Fedorov, A., … Zhizhko, P. A. (2018). Bridging the Gap between Industrial and Well‐Defined Supported Catalysts. Angewandte Chemie International Edition, 57(22), 6398-6440. doi:10.1002/anie.201702387 es_ES
dc.description.references Copéret, C., Allouche, F., Chan, K. W., Conley, M. P., Delley, M. F., Fedorov, A., … Zhizhko, P. A. (2018). Eine Brücke zwischen industriellen und wohldefinierten Trägerkatalysatoren. Angewandte Chemie, 130(22), 6506-6551. doi:10.1002/ange.201702387 es_ES


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