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dc.contributor.authorCasanova González, Noelia
dc.contributor.authordel Rio, Karina P.
dc.contributor.authorGarcía Fandiño, Rebeca
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorGulías Costa, Moisés
dc.date.accessioned2016-09-08T08:08:53Z
dc.date.available2016-09-08T08:08:53Z
dc.date.issued2016-04-14
dc.identifier.citationACS Catal., 2016, 6 (5), pp 3349–3353
dc.identifier.otherE-ISSN 2155-5435
dc.identifier.urihttp://hdl.handle.net/10347/14871
dc.description.abstract2-Alkenylphenols react with allenes, upon treatment with catalytic amounts of Pd(II) and Cu(II), to give benzoxepine products in high yields and with very good regio- and diastereoselectivities. This contrasts with the results obtained with Rh catalysts, which provided chromene-like products through a pathway involving a β-hydrogen elimination step. Computational studies suggest that the square planar geometry of the palladium is critical to favor the reductive elimination process required for the formation of the oxepine products
dc.description.sponsorshipThis work was supported by the Spanish MINECO (grant:SAF2013-41943-R), the ERDF, the European Research Council (Advanced Grant No. 340055) and the Xunta de Galicia (grants: GRC2013-041 and 2015-CP082). We also thank the orfeo-cinqa CTQ2014-51912-REDC. K.P.D.R. thanks the Coordenaça̧o de Aperfeiçoamento de Pessoal de ̧Nıvel Superior (CAPES, Brazil) for the Ph.D scholarship. We ́thank Dr. M. Martınez for XRD analysis. All calculations were ́carried out at Centro de Supercomputación de Galicia (CESGA)
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relationinfo: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.rights© American Chemical Society
dc.subjectAllene
dc.subjectCycloaddition
dc.subjectC-H activation
dc.subjectOxepine
dc.subjectPalladium
dc.subject.classificationMaterias::Investigación::23 Química::2302 Bioquímica
dc.titlePalladium(II)-Catalyzed annulation between ortho-alkenylphenols and allenes. Key role of the metal geometry in determining the reaction outcome
dc.typeinfo:eu-repo/semantics/article
dc.identifier.DOI10.1021/acscatal.6b00739
dc.relation.publisherversionhttp://dx.doi.org/10.1021/acscatal.6b00739
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica


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