Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides

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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 Pérez, Andrea
dc.contributor.authorEsteruelas Rodrigo, Miguel Ángel
dc.contributor.authorIzquierdo, Susana
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2020-10-05T07:05:57Z
dc.date.available2020-10-05T07:05:57Z
dc.date.issued2019
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Álvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350. [doi: 10.1021/acs.orglett.9b01993]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstractComplex CpRuCl(PPh3)2 catalyzes reactions of terminal alkynes with 4-picoline N-oxide and primary and secondary amines to afford the corresponding amides. The reactions occur in chlorinated solvent and aqueous medium, showing applications in peptide chemistry. Stoichiometric studies reveal that the true catalysts of the processes are the vinylidene cations [CpRu(═C═CHR)(PPh3)2]+ which are oxidized to the Ru(η2-CO)-ketenes by the N-oxide. Finally, nucleophilic additions of primary and secondary amines to the free ketenes yield the corresponding amides.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from MINECO (projects CTQ2014-59015R, CTQ2017-87939R, CTQ2017-82935-P and ORFEO-CINQA network CTQ2016-81797-REDC), the Xunta de Ga-licia (project GRC2014/032, ED431C 2018/04, Centro singular de in-vestigación de Galicia accreditation 2016–2019, ED431G/09), DGA (No.E06_17R) and the European Union (European Regional Develop-ment Fund - ERDF). A. A.-P. thanks Spanish MICINN for a predoctoral FPI fellowshipgl
dc.identifier.citationÁlvarez-Pérez, A., Esteruelas, M. A., Izquierdo, S., Varela, J. A., Saá, C. (2019). Ruthenium-Catalyzed Oxidative Amidation of Alkynes to Amides. Org. Lett., 21, 13, 5346-5350gl
dc.identifier.doi10.1021/acs.orglett.9b01993
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/23355
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-59015R/ES/SINTESIS SOSTENIBLE DE FARMACOFOROS HETEROCICLICOS Y GRAFENOS BIFENILENICOS MEDIANTE TRANSFORMACIONES CATALITICAS ORGANOMETALICAS
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.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDC/ES
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.9b01993gl
dc.rightsCopyright © 2019 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.subjectAlkynesgl
dc.subjectAmidesgl
dc.subjectOxidative Annulationgl
dc.subjectRutheniumgl
dc.titleRuthenium-Catalyzed Oxidative Amidation of Alkynes to Amidesgl
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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