Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies

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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.authorÁlvarez-Constantino, Andrés M.
dc.contributor.authorÁlvarez Pérez, Andrea
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSciortino, Giuseppe
dc.contributor.authorUjaque Pérez, Gregori
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2023-03-17T07:25:50Z
dc.date.available2023-03-17T07:25:50Z
dc.date.issued2023
dc.description.abstractThe Ru-catalyzed intramolecular oxidative amidation (lactamization) of aromatic alkynylamines with 4-picoline N-oxide as an external oxidant has been developed. This chemoselective process is very efficient to achieve medium-sized ε- and ζ-lactams (seven- and eight-membered rings) but not for the formation of common δ-lactams (six-membered rings). DFT studies unveiled the capital role of the chain length between the amine and the alkyne functionalities: the longer the connector, the more favored the lactamization process vs hydroamination.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from MICINN (projects PID2020-118048GB-I00, PID2020-116861GB-I00, and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2022/27, Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03), and the European Union (European Regional Development Fund)gl
dc.identifier.citationÁlvarez-Constantino, A., Álvarez-Pérez, A., Varela, J. A., Sciortino, G., Ujaque, G., Saá, C. (2023). Chemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studies. J. Org. Chem., 88, 2, 1185-193gl
dc.identifier.doi10.1021/acs.joc.2c02770
dc.identifier.essn1520-6904
dc.identifier.issn0022-3263
dc.identifier.urihttp://hdl.handle.net/10347/30334
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/PID2020-118048GB-I00/ESgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-116861GB-I00/ES/FRONTERAS EN LA MODELIZACION DE PROCESOS DE CATALISIS Y RECONOMIENTOS MOLECULARES MEDIADOS POR METALES DE TRANSICIONgl
dc.relation.publisherversionhttps://doi.org/10.1021/acs.joc.2c02770gl
dc.rights© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)gl
dc.rights.accessRightsopen accessgl
dc.subjectAlkynylaminesgl
dc.subjectBenzazepinonesgl
dc.subjectMedium-sized lactamsgl
dc.subjectLactamizationsgl
dc.subjectRuthenium catalystsgl
dc.titleChemoselective Ru-Catalyzed Oxidative Lactamization vs Hydroamination of Alkynylamines: Insights from Experimental and Density Functional Theory Studiesgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
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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