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dc.contributor.author | Martínez-Arranz, Sheila | es_ES |
dc.contributor.author | Carrera, Nora | es_ES |
dc.contributor.author | Albéniz, Ana C. | es_ES |
dc.contributor.author | Espinet, Pablo | es_ES |
dc.contributor.author | Vidal Moya, José Alejandro | es_ES |
dc.date.accessioned | 2013-06-10T10:07:22Z | |
dc.date.issued | 2012-12 | |
dc.identifier.issn | 1615-4150 | |
dc.identifier.uri | http://hdl.handle.net/10251/29557 | |
dc.description.abstract | [EN] The Stille coupling can be carried out in a batch process using insoluble tin supports. The new type of support consists of stannylated polymers based on the vinylic polynorbornene skeleton that allow one to use a set-up where the tin reagent is immobilized in a column. The immobilized stannylated polymeric reagent can be easily reused. The coupling products are thus obtained by a very simple work-up procedure and have very low levels of tin contamination. | es_ES |
dc.description.sponsorship | Financial support from the Spanish MEC (DGI, grant CTQ2010-18901/BQU; fellowship to N. C.), and the Junta de Castilla y Leon (grant VA373A11-2) is gratefully acknowledged. | |
dc.language | Inglés | es_ES |
dc.publisher | Wiley-VCH Verlag | es_ES |
dc.relation.ispartof | Advanced Synthesis and Catalysis | es_ES |
dc.rights | Reserva de todos los derechos | es_ES |
dc.subject | C -C coupling | es_ES |
dc.subject | Green chemistry | es_ES |
dc.subject | Polymers | es_ES |
dc.subject | Recycling | es_ES |
dc.subject | Stille reaction | es_ES |
dc.subject | Tin | es_ES |
dc.title | Batch Stille Coupling with Insoluble and Recyclable Stannylated Polynorbornenes | es_ES |
dc.type | Artículo | es_ES |
dc.embargo.lift | 10000-01-01 | |
dc.embargo.terms | forever | es_ES |
dc.identifier.doi | 10.1002/adsc.201200624 | |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//CTQ2010-18901/ES/FORMACION CATALITICA DE ENLACES C-C: ESTUDIOS MECANISICOS, DESARROLLOS SINTETICOS Y DESARROLLOS METODOLOGICOS/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/Junta de Castilla y León//VA373A11-2/ES/REACCIONES PARA LA FORMACIÓN DE ENLACES CŒC: ESTUDIOS MECANÍSTICOS Y DESARROLLO DE NUEVOS CATALIZADORES Y NUEVAS METODOLOGÍA/ | es_ES |
dc.rights.accessRights | Cerrado | 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 | Martínez-Arranz, S.; Carrera, N.; Albéniz, AC.; Espinet, P.; Vidal Moya, JA. (2012). Batch Stille Coupling with Insoluble and Recyclable Stannylated Polynorbornenes. Advanced Synthesis and Catalysis. 354(18):3551-3560. https://doi.org/10.1002/adsc.201200624 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | http://dx.doi.org/10.1002/adsc.201200624 | es_ES |
dc.description.upvformatpinicio | 3551 | es_ES |
dc.description.upvformatpfin | 3560 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 354 | es_ES |
dc.description.issue | 18 | es_ES |
dc.relation.senia | 239788 | |
dc.contributor.funder | Junta de Castilla y León | |
dc.contributor.funder | Ministerio de Ciencia e Innovación | es_ES |
dc.description.references | Scully, S. S., & Porco, J. A. (2011). Asymmetric Total Synthesis of the Epoxykinamycin FL-120 B′. Angewandte Chemie, 123(41), 9896-9900. doi:10.1002/ange.201104504 | es_ES |
dc.description.references | Scully, S. S., & Porco, J. A. (2011). Asymmetric Total Synthesis of the Epoxykinamycin FL-120 B′. Angewandte Chemie International Edition, 50(41), 9722-9726. doi:10.1002/anie.201104504 | es_ES |
dc.description.references | Carsten, B., He, F., Son, H. J., Xu, T., & Yu, L. (2011). Stille Polycondensation for Synthesis of Functional Materials. Chemical Reviews, 111(3), 1493-1528. doi:10.1021/cr100320w | es_ES |
dc.description.references | Lu, S., Xu, Z., Bao, M., & Yamamoto, Y. (2008). Carbocycle Synthesis through Facile and Efficient Palladium-Catalyzed Allylative De-aromatization of Naphthalene and Phenanthrene Allyl Chlorides. Angewandte Chemie, 120(23), 4438-4441. doi:10.1002/ange.200800529 | es_ES |
dc.description.references | Lu, S., Xu, Z., Bao, M., & Yamamoto, Y. (2008). Carbocycle Synthesis through Facile and Efficient Palladium-Catalyzed Allylative De-aromatization of Naphthalene and Phenanthrene Allyl Chlorides. Angewandte Chemie International Edition, 47(23), 4366-4369. doi:10.1002/anie.200800529 | es_ES |
dc.description.references | Li, J., Lutz, M., Spek, A. L., van Klink, G. P. M., van Koten, G., & Klein Gebbink, R. J. M. (2010). Chiral Amino Alcohol Derived Bis-phosphoramidite Pincer Palladium Complexes and Their Applications in Asymmetric Allylation of Aldimines. Organometallics, 29(6), 1379-1387. doi:10.1021/om100021p | es_ES |
dc.description.references | Lam, H. W., & Pattenden, G. (2002). Total Synthesis of the Presumed Amphidinolide A. Angewandte Chemie, 114(3), 526-529. doi:10.1002/1521-3757(20020201)114:3<526::aid-ange526>3.0.co;2-m | es_ES |
dc.description.references | Lam, H. W., & Pattenden, G. (2002). Total Synthesis of the Presumed Amphidinolide A. Angewandte Chemie International Edition, 41(3), 508-511. doi:10.1002/1521-3773(20020201)41:3<508::aid-anie508>3.0.co;2-7 | es_ES |
dc.description.references | Powell, D. A., Maki, T., & Fu, G. C. (2005). Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents. Journal of the American Chemical Society, 127(2), 510-511. doi:10.1021/ja0436300 | es_ES |
dc.description.references | Herve, A., Rodriguez, A. L., & Fouquet, E. (2005). Stille Cross-Coupling of Activated Alkyltin Reagents under «Ligandless» Conditions. The Journal of Organic Chemistry, 70(5), 1953-1956. doi:10.1021/jo047907q | es_ES |
dc.description.references | Chiappe, C., Imperato, G., Napolitano, E., & Pieraccini, D. (2004). Ligandless Stille cross-coupling in ionic liquidsElectronic supplementary information (ESI) available: Stille coupling of iodobenzene with tributylvinylstannane in ionic liquids with complexed palladium catalyst. See http://www.rsc.org/suppdata/gc/b3/b313221h/. Green Chemistry, 6(1), 33. doi:10.1039/b313221h | es_ES |
dc.description.references | Gallagher, W. P., & Maleczka, R. E. (2005). Stille Reactions Catalytic in Tin: A «Sn−F» Route for Intermolecular and Intramolecular Couplings†. The Journal of Organic Chemistry, 70(3), 841-846. doi:10.1021/jo0484169 | es_ES |
dc.description.references | Gallagher, W. P., Terstiege, I., & Maleczka, R. E. (2001). Stille Couplings Catalytic in Tin: The «Sn−O» Approach. Journal of the American Chemical Society, 123(14), 3194-3204. doi:10.1021/ja0035295 | es_ES |
dc.description.references | Olofsson, K., Kim, S.-Y., Larhed, M., Curran, D. P., & Hallberg, A. (1999). High-Speed, Highly Fluorous Organic Reactions. The Journal of Organic Chemistry, 64(12), 4539-4541. doi:10.1021/jo982511y | es_ES |
dc.description.references | Stien, D., & Gastaldi, S. (2004). Design of Polyaromatic Hydrocarbon-Supported Tin Reagents: A New Family of Tin Reagents Easily Removable from Reaction Mixtures. The Journal of Organic Chemistry, 69(13), 4464-4470. doi:10.1021/jo049868o | es_ES |
dc.description.references | Leibner, J. E., & Jacobus, J. (1979). Facile product isolation from organostannane reductions of organic halides. The Journal of Organic Chemistry, 44(3), 449-450. doi:10.1021/jo01317a032 | es_ES |
dc.description.references | Harrowven, D. C., & Guy, I. L. (2004). KF–Silica as a stationary phase for the chromatographic removal of tin residues from organic compounds. Chem. Commun., (17), 1968-1969. doi:10.1039/b406041e | es_ES |
dc.description.references | Harrowven, D. C., Curran, D. P., Kostiuk, S. L., Wallis-Guy, I. L., Whiting, S., Stenning, K. J., … Nanson, L. (2010). Potassium carbonate–silica: a highly effective stationary phase for the chromatographic removal of organotin impurities. Chemical Communications, 46(34), 6335. doi:10.1039/c0cc01328e | es_ES |
dc.description.references | Kerric, G., Le Grognec, E., Zammattio, F., Paris, M., & Quintard, J.-P. (2010). Use of polymer-supported phenyltin for the creation of aryl–aryl or aryl–heteroaryl bonds via Stille cross-coupling reactions. Journal of Organometallic Chemistry, 695(1), 103-110. doi:10.1016/j.jorganchem.2009.09.034 | es_ES |
dc.description.references | Chrétien, J.-M., Mallinger, A., Zammattio, F., Grognec, E. L., Paris, M., Montavon, G., & Quintard, J.-P. (2007). Evaluation of polymer-supported vinyltin reagents in the Stille cross-coupling reaction. Tetrahedron Letters, 48(10), 1781-1785. doi:10.1016/j.tetlet.2007.01.028 | es_ES |
dc.description.references | Nicolaou, K. C., Winssinger, N., Pastor, J., & Murphy, F. (1998). Festphasensynthese von Makrocyclen mit der Strategie der Abspaltung unter Cyclisierung: Anwendung der Stille-Kupplung bei der Synthese von (S)-Zearalenon. Angewandte Chemie, 110(18), 2677-2680. doi:10.1002/(sici)1521-3757(19980918)110:18<2677::aid-ange2677>3.0.co;2-c | es_ES |
dc.description.references | Nicolaou, K. C., Winssinger, N., Pastor, J., & Murphy, F. (1998). Solid-Phase Synthesis of Macrocyclic Systems by a Cyclorelease Strategy: Application of the Stille Coupling to a Synthesis of (S)-Zearalenone. Angewandte Chemie International Edition, 37(18), 2534-2537. doi:10.1002/(sici)1521-3773(19981002)37:18<2534::aid-anie2534>3.0.co;2-f | es_ES |
dc.description.references | Kuhn, H., & Neumann, W. P. (1994). Investigations on the Stille Reaction Carried Out with Polymer-Supported Organotin Reagents. Synlett, 1994(02), 123-124. doi:10.1055/s-1994-22763 | es_ES |
dc.description.references | Meana, I., Albéniz, A. C., & Espinet, P. (2010). Selective Green Coupling of Alkynyltins and Allylic Halides to Trienynes via a Tandem Double Stille Reaction. Advanced Synthesis & Catalysis, 352(17), 2887-2891. doi:10.1002/adsc.201000430 | es_ES |
dc.description.references | Carrera, N., Gutiérrez, E., Benavente, R., Villavieja, M. M., Albéniz, A. C., & Espinet, P. (2008). Stannylated Polynorbornenes as New Reagents for a Clean Stille Reaction. Chemistry - A European Journal, 14(32), 10141-10148. doi:10.1002/chem.200800558 | es_ES |
dc.description.references | Carrera, N., Salinas-Castillo, A., Albéniz, A. C., Espinet, P., & Mallavia, R. (2011). Fluorene-based stannylated polymers and their use as recyclable reagents in the Stille reaction. Journal of Organometallic Chemistry, 696(21), 3316-3321. doi:10.1016/j.jorganchem.2011.07.004 | es_ES |
dc.description.references | Louaisil, N., Pham, P. D., Boeda, F., Faye, D., Castanet, A.-S., & Legoupy, S. (2010). Ionic Liquid Supported Organotin Reagents: Green Tools for Stille Cross-Coupling Reactions with Brominated Substrates. European Journal of Organic Chemistry, 2011(1), 143-149. doi:10.1002/ejoc.201001195 | es_ES |
dc.description.references | Dien Pham, P., Vitz, J., Chamignon, C., Martel, A., & Legoupy, S. (2009). Stille Cross-Coupling Reactions with Tin Reagents Supported on Ionic Liquids. European Journal of Organic Chemistry, 2009(19), 3249-3257. doi:10.1002/ejoc.200900177 | es_ES |
dc.description.references | Vitz, J., Mac, D. H., & Legoupy, S. (2007). Ionic liquid supported tin reagents for Stille cross coupling reactions. Green Chemistry, 9(5), 431. doi:10.1039/b616218e | es_ES |
dc.description.references | Martínez-Arranz, S., Albéniz, A. C., & Espinet, P. (2010). Versatile Route to Functionalized Vinylic Addition Polynorbornenes. Macromolecules, 43(18), 7482-7487. doi:10.1021/ma101137z | es_ES |
dc.description.references | White, D. C. (1961). Micro determination of chlorine or bromine in organic compounds. Mikrochimica Acta, 49(3), 449-456. doi:10.1007/bf01217477 | es_ES |
dc.description.references | Casares, J. A., Espinet, P., Martín-Alvarez, J. M., Martínez-Ilarduya, J. M., & Salas, G. (2005). Stable Nickel Catalysts for Fast Norbornene Polymerization: Tuning Reactivity. European Journal of Inorganic Chemistry, 2005(19), 3825-3831. doi:10.1002/ejic.200500121 | es_ES |
dc.description.references | Chu, P. ., Huang, W.-J., Chang, F. ., & Fan, S. . (2000). Conformational conversion and chain ordering in cyclo olefin copolymer (COC). Polymer, 41(1), 401-404. doi:10.1016/s0032-3861(99)00450-4 | es_ES |
dc.description.references | Kaminsky, W., Bark, A., & Arndt, M. (1991). New polymers by homogenous zirconocene/aluminoxane catalysts. Makromolekulare Chemie. Macromolecular Symposia, 47(1), 83-93. doi:10.1002/masy.19910470108 | es_ES |
dc.description.references | Arndt, M., Engehausen, R., Kaminsky, W., & Zoumis, K. (1995). Hydrooligomerization of cycloolefins -a view of the microstructure of polynorbornene. Journal of Molecular Catalysis A: Chemical, 101(3), 171-178. doi:10.1016/1381-1169(95)00083-6 | es_ES |
dc.description.references | Carrera, N., Pérez-Temprano, M. H., Albéniz, A. C., Casares, J. A., & Espinet, P. (2009). A Convenient Quick Synthesis of SnBu2RCl Derivatives. Organometallics, 28(13), 3957-3958. doi:10.1021/om900326g | es_ES |
dc.description.references | Hill, E. A., Hsieh, K., Condroski, K., Sonnentag, H., Skalitzky, D., & Gagas, D. (1989). Rearrangement and cleavage of the Grignard reagent from 5-(chloromethyl)norbornene. The Journal of Organic Chemistry, 54(22), 5286-5292. doi:10.1021/jo00283a022 | es_ES |
dc.description.references | Usón, R., Forniés, J., Nalda, J. A., Lozano, M. J., Espinet, P., & Albéniz, A. C. (1989). Synthesis of (NBu4)2[Pd2(μ-Br)2(C6X5)2Br2] (X=F, Cl), new and more versatile precursors of pentahalophenyl derivatives of palladium(II). Inorganica Chimica Acta, 156(2), 251-256. doi:10.1016/s0020-1693(00)83508-2 | es_ES |
dc.description.references | Albéniz, A. C., Espinet, P., & López-Fernández, R. (2003). Polymerization of Acrylates by Neutral Palladium Complexes. Isolation of Complexes at the Initial Steps. Organometallics, 22(21), 4206-4212. doi:10.1021/om030507t | es_ES |
dc.description.references | Coulson, D. R., Satek, L. C., & Grim, S. O. (2007). Tetrakis(Triphenylphosphine)Palladium(0). Inorganic Syntheses, 107-109. doi:10.1002/9780470132593.ch28 | es_ES |
dc.description.references | Echavarren, A. M., & Stille, J. K. (1987). Palladium-catalyzed coupling of aryl triflates with organostannanes. Journal of the American Chemical Society, 109(18), 5478-5486. doi:10.1021/ja00252a029 | es_ES |
dc.description.references | Gomes, P., Gosmini, C., & Périchon, J. (2003). Cobalt-Catalyzed Direct Electrochemical Cross-Coupling between Aryl or Heteroaryl Halides and Allylic Acetates or Carbonates. The Journal of Organic Chemistry, 68(3), 1142-1145. doi:10.1021/jo026421b | es_ES |
dc.description.references | Haley, R. C., Miller, J. A., & Wood, H. C. S. (1969). Phosphate esters. Part II. The formation of monoterpene hydrocarbons from geranyl and neryl diphenyl phosphates. Journal of the Chemical Society C: Organic, (2), 264. doi:10.1039/j39690000264 | es_ES |
dc.description.references | Chen, Q. Y., & Li, Z. T. (1993). Pentafluorophenylation of aromatics with pentafluorophenyl perfluoro- and polyfluoroalkanesulfonates. A photoinduced electron-transfer cation diradical coupling process. The Journal of Organic Chemistry, 58(9), 2599-2604. doi:10.1021/jo00061a041 | es_ES |
dc.description.references | Stefani, H. A., Pena, J. M., Manarin, F., Ando, R. A., Leal, D. M., & Petragnani, N. (2011). Negishi cross-coupling of organotellurium compounds: synthesis of biaryls, aryl-, and diaryl acetylenes. Tetrahedron Letters, 52(34), 4398-4401. doi:10.1016/j.tetlet.2011.06.025 | es_ES |
dc.description.references | Denmark, S. E., Smith, R. C., & Tymonko, S. A. (2007). Phosphine oxides as stabilizing ligands for the palladium-catalyzed cross-coupling of potassium aryldimethylsilanolates. Tetrahedron, 63(26), 5730-5738. doi:10.1016/j.tet.2007.02.017 | es_ES |
dc.description.references | Leowanawat, P., Zhang, N., Resmerita, A.-M., Rosen, B. M., & Percec, V. (2011). Ni(COD)2/PCy3Catalyzed Cross-Coupling of Aryl and Heteroaryl Neopentylglycolboronates with Aryl and Heteroaryl Mesylates and Sulfamates in THF at Room Temperature. The Journal of Organic Chemistry, 76(24), 9946-9955. doi:10.1021/jo202037x | es_ES |
dc.description.references | Kulp, S. S., & McGee, M. J. (1983). Oxidative decyanation of benzyl and benzhydryl cyanides. A simplified procedure. The Journal of Organic Chemistry, 48(22), 4097-4098. doi:10.1021/jo00170a044 | es_ES |
dc.description.references | Matsubara, R., Gutierrez, A. C., & Jamison, T. F. (2011). Nickel-Catalyzed Heck-Type Reactions of Benzyl Chlorides and Simple Olefins. Journal of the American Chemical Society, 133(47), 19020-19023. doi:10.1021/ja209235d | es_ES |