- -

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

RiuNet: Repositorio Institucional de la Universidad Politécnica de Valencia

Compartir/Enviar a

Citas

Estadísticas

  • Estadisticas de Uso

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

Mostrar el registro completo del ítem

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

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/165285

Ficheros en el ítem

Thumbnail
Nombre: Rvero-Crespo;Teje ...
Tamaño: 624.8Kb
Formato: PDF
Descripción: Versión del Autor.
Abrir/Preview
[Cerrado]
Nombre: anie.201909597.pdf
Tamaño: 1.863Mb
Formato: PDF
Descripción: Versión editorial
Solicitar una copia al autor

Metadatos del ítem

Título: Intermolecular Carbonyl-olefin Metathesis with Vinyl Ethers Catalyzed by Homogeneous and Solid Acids in Flow
Autor: Rivero-Crespo, Miguel Ángel Tejeda-Serrano, Maria Perez-Sánchez, Horacio Cerón-Carrasco, José Pedro Leyva Perez, Antonio
Entidad UPV: Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química
Fecha difusión:
Resumen:
[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 ...[+]
Palabras clave: Carbonyl-olefin metathesis , Heterogeneous catalysis , In-flow reactions , Montmorillonite K10 , Vinyl ethers
Derechos de uso: Reserva de todos los derechos
Fuente:
Angewandte Chemie International Edition. (issn: 1433-7851 )
DOI: 10.1002/anie.201909597
Editorial:
John Wiley & Sons
Versión del editor: https://doi.org/10.1002/anie.201909597
Código del Proyecto:
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./
info:eu-repo/grantAgreement/AEI//RTC-2017-6331-5/ES/NUEVA SINTESIS DEL OLIGOMERO CLAVE EN TINTAS DIGITALES/
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/
info:eu-repo/grantAgreement/MINECO//SEV-2016-0683/
Descripción: 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.
Agradecimientos:
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 ...[+]
Tipo: Artículo

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

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

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 [+]
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

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

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

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

For reviews on carbonyl olefin metathesis see:

Schindler, C., & Ludwig, J. (2017). Lewis Acid Catalyzed Carbonyl–Olefin Metathesis. Synlett, 28(13), 1501-1509. doi:10.1055/s-0036-1588827

T. H. Lambert Synlett2019 ahead of print.

For examples of solid-catalyzed low-temperature alkene metathesis see:

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

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

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

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

For pure Bronsted acid-catalyzed reactions see:

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

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

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

For intermolecular reactions see:

Ni, S., & Franzén, J. (2018). Carbocation catalysed ring closing aldehyde–olefin metathesis. Chemical Communications, 54(92), 12982-12985. doi:10.1039/c8cc06734a

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

D’Auria, M., & Racioppi, R. (2013). Oxetane Synthesis through the Paternò-Büchi Reaction. Molecules, 18(9), 11384-11428. doi:10.3390/molecules180911384

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

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

Prantz, K., & Mulzer, J. (2010). Synthetic Applications of the Carbonyl Generating Grob Fragmentation. Chemical Reviews, 110(6), 3741-3766. doi:10.1021/cr900386h

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

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

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

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

[-]

recommendations

 

Este ítem aparece en la(s) siguiente(s) colección(ones)

Mostrar el registro completo del ítem