Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Molecularesgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorCendón Mariño, Borja
dc.contributor.authorCasanova González, Noelia
dc.contributor.authorComanescu, Cezar
dc.contributor.authorGarcía Fandiño, Rebeca
dc.contributor.authorSeoane Fernández, Andrés
dc.contributor.authorGulías Costa, Moisés
dc.contributor.authorMascareñas Cid, José Luis
dc.date.accessioned2017-05-31T12:22:03Z
dc.date.available2018-03-27T01:00:11Z
dc.date.issued2017-03-27
dc.descriptionThis is the peer reviewed version of the following article: Borja Cendón, Noelia Casanova, Cezar Comanescu, Rebeca García-Fandiño, Andrés Seoane, Moisés Gulías* and José L. Mascareñas*, Palladium-Catalyzed Formal (5+2) annulation between ortho-Alkenylanilides and Allenes. Org. Lett. 2017, 19, 1674-1677 [DOI: ]. This article may be used for non commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstract2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C–H activation of the alkenylanilide involves a classical concerted metalation–deprotonation (CMD) mechanismgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from Spanish grants (SAF2013-41943-R, SAF2016-76689-R, CTQ2015-74621-JIN and CTQ2016-77047-P), the Consellería de Cultura, Educación e Ordenación Universitaria (GRC2013-041, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2016-2019, ED431G/09), the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055). R. G.-F. thanks a FCT scholarship from Portugal. The orfeo-cinqa network CTQ2014-51912-REDC is kindly acknowledged. All calculations were carried out at Centro de Supercomputación de Galicia (CESGA)gl
dc.identifier.citationCendón, B., Casanova, N., Comanescu, C., Garcí­a-Fandiño, R., Seoane, A., Gulías, M. & Mascareñas, J.L. 2017, "Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes", Organic letters, vol. 19, no. 7, pp. 1674-1677gl
dc.identifier.doi10.1021/acs.orglett.7b00467
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/15444
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-74621-JIN/ES/DISEÑO DE BIOCIDAS INNOVADORES A PARTIR DE LA ELUCIDACION DEL MECANISMO DE OLIGOMEROS CON PROPIEDADES ANTIMICROBIANAS
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2013-41943-R/ES/HERRAMIENTAS SINTETICAS EN QUIMICA BIOLOGICA. NUEVAS ESTRATEGIAS MOLECULARES PARA EL TRATAMIENTO Y DIAGNOSTICO DE CANCERES
dc.relation.publisherversionhttp://dx.doi.org/10.1021/acs.orglett.7b00467gl
dc.rights© 2017 American Chemical Societygl
dc.rights.accessRightsopen accessgl
dc.subjectPalladium-catalyzedgl
dc.subjectOrtho- alkenylanilidesgl
dc.subjectAllenesgl
dc.subject.classificationMaterias::Investigación::23 Química::2302 Bioquímicagl
dc.titlePalladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenesgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
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