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Deactivation of Cationic Cu-I and Au-I Catalysts for A(3) Coupling by CH2Cl2 : Mechanistic Implications of the Formation of Neutral Cu-I and Au-I Chlorides

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Deactivation of Cationic Cu-I and Au-I Catalysts for A(3) Coupling by CH2Cl2 : Mechanistic Implications of the Formation of Neutral Cu-I and Au-I Chlorides

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dc.contributor.author Grirrane ., Abdessamad es_ES
dc.contributor.author Álvarez, Eleuterio es_ES
dc.contributor.author García Gómez, Hermenegildo es_ES
dc.contributor.author Corma Canós, Avelino es_ES
dc.date.accessioned 2016-01-18T09:50:46Z
dc.date.issued 2014-07
dc.identifier.issn 1433-7851
dc.identifier.uri http://hdl.handle.net/10251/59971
dc.description.abstract Care should be exercised when using CH2Cl2 as a solvent for reactions in which amines are a reagent, since undesirable deactivation of cationic copper(I) and gold( I) catalysts to form the corresponding inactive neutral chloride complexes [LMCl] (M=Cu or Au) can occur as a result of the generation of hydrogen chloride in the medium. Cu-I and Au-I deactivation has been proved for the Mannich three-component coupling reaction. A series of CuI and AuI complexes with potential mechanistic implications were isolated and characterized by X-ray crystallography. es_ES
dc.description.sponsorship Financial support by the Spanish Ministry of the Economy and Competitiveness (Severo Ochoa and CTQ2012-32315) and the Generalidad Valenciana (Prometeo 2012-014) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation.ispartof Angewandte Chemie International Edition es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject coordination chemistry es_ES
dc.subject copper intermediates es_ES
dc.subject gold intermediates es_ES
dc.subject homogeneous catalysis es_ES
dc.subject propargylamines es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Deactivation of Cationic Cu-I and Au-I Catalysts for A(3) Coupling by CH2Cl2 : Mechanistic Implications of the Formation of Neutral Cu-I and Au-I Chlorides es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/anie.201403973
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2012-32315/ES/REDUCCION FOTOCATALITICA DEL DIOXIDO DE CARBONO/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//GV%2F2012%2F014/ 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.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Grirrane ., A.; Álvarez, E.; García Gómez, H.; Corma Canós, A. (2014). Deactivation of Cationic Cu-I and Au-I Catalysts for A(3) Coupling by CH2Cl2 : Mechanistic Implications of the Formation of Neutral Cu-I and Au-I Chlorides. Angewandte Chemie International Edition. 53(28):7253-7258. https://doi.org/10.1002/anie.201403973 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1002/anie.201403973 es_ES
dc.description.upvformatpinicio 7253 es_ES
dc.description.upvformatpfin 7258 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 53 es_ES
dc.description.issue 28 es_ES
dc.relation.senia 282053 es_ES
dc.identifier.eissn 1521-3773
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.description.references Hashmi, A. S. K. (2007). Gold-Catalyzed Organic Reactions. Chemical Reviews, 107(7), 3180-3211. doi:10.1021/cr000436x es_ES
dc.description.references Gorin, D. J., Sherry, B. D., & Toste, F. D. (2008). Ligand Effects in Homogeneous Au Catalysis. Chemical Reviews, 108(8), 3351-3378. doi:10.1021/cr068430g es_ES
dc.description.references Fürstner, A. (2009). Gold and platinum catalysis—a convenient tool for generating molecular complexity. Chemical Society Reviews, 38(11), 3208. doi:10.1039/b816696j es_ES
dc.description.references Corma, A., Leyva-Pérez, A., & Sabater, M. J. (2011). Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions. Chemical Reviews, 111(3), 1657-1712. doi:10.1021/cr100414u es_ES
dc.description.references Boorman, T. C., & Larrosa, I. (2011). Gold-mediated C–H bond functionalisation. Chem. Soc. Rev., 40(4), 1910-1925. doi:10.1039/c0cs00098a es_ES
dc.description.references Jiménez-Núñez, E., & Echavarren, A. M. (2008). Gold-Catalyzed Cycloisomerizations of Enynes: A Mechanistic Perspective. Chemical Reviews, 108(8), 3326-3350. doi:10.1021/cr0684319 es_ES
dc.description.references Yoshikai, N., & Nakamura, E. (2011). Mechanisms of Nucleophilic Organocopper(I) Reactions. Chemical Reviews, 112(4), 2339-2372. doi:10.1021/cr200241f es_ES
dc.description.references Surry, D. S., & Buchwald, S. L. (2010). Diamine ligands in copper-catalyzed reactions. Chemical Science, 1(1), 13. doi:10.1039/c0sc00107d es_ES
dc.description.references Ley, S. V., & Thomas, A. W. (2003). Moderne Synthesemethoden: Kupfer-vermittelte C(Aryl)-O-, C(Aryl)-N- und C(Aryl)-S-Verknüpfungen. Angewandte Chemie, 115(44), 5558-5607. doi:10.1002/ange.200300594 es_ES
dc.description.references Ley, S. V., & Thomas, A. W. (2003). Modern Synthetic Methods for Copper-Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation. Angewandte Chemie International Edition, 42(44), 5400-5449. doi:10.1002/anie.200300594 es_ES
dc.description.references Casitas, A., & Ribas, X. (2013). The role of organometallic copper(iii) complexes in homogeneous catalysis. Chemical Science, 4(6), 2301. doi:10.1039/c3sc21818j es_ES
dc.description.references Surry, D. S., & Buchwald, S. L. (2008). Biarylphosphanliganden in der palladiumkatalysierten Aminierung. Angewandte Chemie, 120(34), 6438-6461. doi:10.1002/ange.200800497 es_ES
dc.description.references Surry, D. S., & Buchwald, S. L. (2008). Biaryl Phosphane Ligands in Palladium-Catalyzed Amination. Angewandte Chemie International Edition, 47(34), 6338-6361. doi:10.1002/anie.200800497 es_ES
dc.description.references Bieber, L. W., & da Silva, M. F. (2004). Mild and efficient synthesis of propargylamines by copper-catalyzed Mannich reaction. Tetrahedron Letters, 45(45), 8281-8283. doi:10.1016/j.tetlet.2004.09.079 es_ES
dc.description.references Park, S. B., & Alper, H. (2005). An efficient synthesis of propargylamines via C–H activation catalyzed by copper(i) in ionic liquids. Chem. Commun., (10), 1315-1317. doi:10.1039/b416268d es_ES
dc.description.references Buckley, B. R., Khan, A. N., & Heaney, H. (2012). Mannich Reactions of Alkynes: Mechanistic Insights and the Role of Sub-Stoichiometric Amounts of Alkynylcopper(I) Compounds in the Catalytic Cycle. Chemistry - A European Journal, 18(13), 3855-3858. doi:10.1002/chem.201103987 es_ES
dc.description.references Lo, V. K.-Y., Liu, Y., Wong, M.-K., & Che, C.-M. (2006). Gold(III) Salen Complex-Catalyzed Synthesis of Propargylamines via a Three-Component Coupling Reaction. Organic Letters, 8(8), 1529-1532. doi:10.1021/ol0528641 es_ES
dc.description.references Rach, S. F., & Kühn, F. E. (2009). Nitrile Ligated Transition Metal Complexes with Weakly Coordinating Counteranions and Their Catalytic Applications. Chemical Reviews, 109(5), 2061-2080. doi:10.1021/cr800270h es_ES
dc.description.references Pérez-Galán, P., Delpont, N., Herrero-Gómez, E., Maseras, F., & Echavarren, A. M. (2010). Metal-Arene Interactions in Dialkylbiarylphosphane Complexes of Copper, Silver, and Gold. Chemistry - A European Journal, 16(18), 5324-5332. doi:10.1002/chem.200903507 es_ES
dc.description.references Grirrane, A., Garcia, H., Corma, A., & Álvarez, E. (2013). Air-Stable, Dinuclear and Tetranuclear σ,π-Acetylide Gold(I) Complexes and Their Catalytic Implications. Chemistry - A European Journal, 19(37), 12239-12244. doi:10.1002/chem.201301623 es_ES
dc.description.references Herrero-Gómez, E., Nieto-Oberhuber, C., López, S., Benet-Buchholz, J., & Echavarren, A. M. (2006). Cationic η1/η2-Gold(I) Complexes of Simple Arenes. Angewandte Chemie, 118(33), 5581-5585. doi:10.1002/ange.200601688 es_ES
dc.description.references Herrero-Gómez, E., Nieto-Oberhuber, C., López, S., Benet-Buchholz, J., & Echavarren, A. M. (2006). Cationic η1/η2-Gold(I) Complexes of Simple Arenes. Angewandte Chemie International Edition, 45(33), 5455-5459. doi:10.1002/anie.200601688 es_ES
dc.description.references Yu, D., & Zhang, Y. (2011). Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines. Advanced Synthesis & Catalysis, 353(1), 163-169. doi:10.1002/adsc.201000691 es_ES
dc.description.references Pang, T., Lu, H., & Pang, T. (2009). 1-(3-Phenylprop-2-ynyl)pyrrolidinium chloride. Acta Crystallographica Section E Structure Reports Online, 65(11), o2806-o2806. doi:10.1107/s1600536809042329 es_ES
dc.description.references Homs, A., Escofet, I., & Echavarren, A. M. (2013). On the Silver Effect and the Formation of Chloride-Bridged Digold Complexes. Organic Letters, 15(22), 5782-5785. doi:10.1021/ol402825v es_ES
dc.description.references Grirrane, A., Garcia, H., Corma, A., & Álvarez, E. (2011). Intermolecular [2 + 2] Cycloaddition of Alkyne-Alkene Catalyzed by Au(I) Complexes. What Are the Catalytic Sites Involved? ACS Catalysis, 1(12), 1647-1653. doi:10.1021/cs2004278 es_ES
dc.description.references Mills, J. E., Maryanoff, C. A., Cosgrove, R. M., Scott, L., & McComsey, D. F. (1984). THE REACTION OF AMINES WITH METHYLENE CHLORIDE. A BRIEF REVIEW. Organic Preparations and Procedures International, 16(2), 97-114. doi:10.1080/00304948409356172 es_ES
dc.description.references Federsel, H. J., Koenberg, E., Lilljequist, L., & Swahn, B. M. (1990). Dichloromethane as reactant in synthesis: an expedient transformation of prolinamide to a novel pyrrolo[1,2-c]imidazolone. The Journal of Organic Chemistry, 55(7), 2254-2256. doi:10.1021/jo00294a056 es_ES
dc.description.references Mills, J. E., Maryanoff, C. A., McComsey, D. F., Stanzione, R. C., & Scott, L. (1987). Reaction of amines with methylene chloride. Evidence for rapid aminal formation from N-methylenepyrrolidinium chloride and pyrrolidine. The Journal of Organic Chemistry, 52(9), 1857-1859. doi:10.1021/jo00385a038 es_ES
dc.description.references Gao, J., Song, Q.-W., He, L.-N., Yang, Z.-Z., & Dou, X.-Y. (2012). Efficient iron(iii)-catalyzed three-component coupling reaction of alkynes, CH2Cl2 and amines to propargylamines. Chemical Communications, 48(14), 2024. doi:10.1039/c2cc17616e es_ES
dc.description.references Pattacini, R., Jie, S., & Braunstein, P. (2009). Facile dichloromethane activation and phosphine methylation. Isolation of unprecedented zwitterionic organozinc and organocobalt intermediates. Chemical Communications, (8), 890. doi:10.1039/b817728g es_ES
dc.description.references Brunet, J.-J., Couillens, X., Daran, J.-C., Diallo, O., Lepetit, C., & Neibecker, D. (1998). Activation of Dichloromethane by (Phosphane)orhodium(I) Complexes − X-ray Structure of [{(PEt3)2RhCl}2(μ-Cl)2(μ-CH2)]. European Journal of Inorganic Chemistry, 1998(3), 349-353. doi:10.1002/(sici)1099-0682(199803)1998:3<349::aid-ejic349>3.0.co;2-5 es_ES
dc.description.references Yan, T.-H., Tsai, C.-C., Chien, C.-T., Cho, C.-C., & Huang, P.-C. (2004). Dichloromethane Activation. Direct Methylenation of Ketones and Aldehydes with CH2Cl2Promoted by Mg/TiCl4/THF. Organic Letters, 6(26), 4961-4963. doi:10.1021/ol0478887 es_ES
dc.description.references Michelet, V., Toullec, P. Y., & Genêt, J.-P. (2008). Cycloisomerisierungen von 1,n-Eninen: faszinierende metallkatalysierte Umlagerungen und mechanistische Einblicke. Angewandte Chemie, 120(23), 4338-4386. doi:10.1002/ange.200701589 es_ES
dc.description.references Michelet, V., Toullec, P. Y., & Genêt, J.-P. (2008). Cycloisomerization of 1,n-Enynes: Challenging Metal-Catalyzed Rearrangements and Mechanistic Insights. Angewandte Chemie International Edition, 47(23), 4268-4315. doi:10.1002/anie.200701589 es_ES
dc.description.references Rudolph, M., & Hashmi, A. S. K. (2012). Gold catalysis in total synthesis—an update. Chem. Soc. Rev., 41(6), 2448-2462. doi:10.1039/c1cs15279c es_ES


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