Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines

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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.authorVelasco Rubio, Álvaro
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2020-10-05T07:14:06Z
dc.date.available2021-05-01T01:00:15Z
dc.date.issued2020
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Velasco-Rubio, A., Varela, J. A., Saá, C. (2020). Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines. Org. Lett., 22, 9, 3591-3595. [doi: 10.1021/acs.orglett.0c01053]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstractPhenethyltriflamides react with 1,3-dienes upon treatment with a catalytic amount of Pd(OAc)2 and Cu(OAc)2/O2 as oxidant to afford chemo-, regio- and diastereoselectively 2,3,4,5-tetrahydro-1H-benzo[d]azepines (3-benzazepine derivatives) in good to excellent yields. A DFT study of the [5+2] heteroannulation suggests a mechanistic pathway starting by the formation of the six-membered palladacycle cis-PdX2L2 via a CMD process followed by η2 coordination and insertion of the 1,3-diene unit in a diastereoselective manner.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). A.V.-R. thanks Xunta de Galicia for a predoctoral fel-lowship (ED481A-2018/34, 2018-2021)gl
dc.identifier.citationVelasco-Rubio, A., Varela, J. A., Saá, C. (2020). Palladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepines. Org. Lett., 22, 9, 3591-3595gl
dc.identifier.doi10.1021/acs.orglett.0c01053
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/23358
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-87939-R/ES/NUEVAS RUTAS CATALITICAS A PAHS (HIDROCARBUROS AROMATICOS POLICICLICOS) DOPADOS Y HETEROCICLOS BIOACTIVOS
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.0c01053gl
dc.rightsCopyright © 2020 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.rights.accessRightsopen accessgl
dc.subject3-Benzazepinesgl
dc.subject1,3-Dienesgl
dc.subject[5+2] Heteroannulationgl
dc.subjectPalladiumgl
dc.subjectPhenethylamidesgl
dc.titlePalladium-Catalyzed [5+2] Heteroannulation of Phenethylamides with 1,3-Dienes to Dopaminergic 3-Benzazepinesgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
relation.isAuthorOfPublicatione9be05f9-b5a3-405c-aaf6-4e32700dd21d
relation.isAuthorOfPublication2c024eb2-7698-4785-bd0c-518f70068330
relation.isAuthorOfPublication.latestForDiscoverye9be05f9-b5a3-405c-aaf6-4e32700dd21d

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