Rh(III)-Catalyzed [5+2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT

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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.authorMartínez Yáñez, Nuria
dc.contributor.authorSuárez Rivero, Jaime
dc.contributor.authorCajaraville Leiro, Ana
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2020-10-05T07:03:44Z
dc.date.available2020-10-05T07:03:44Z
dc.date.issued2019
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Martínez-Yáñez, N., Suárez, J., Cajaraville, A., Varela, J. A., Saá, C. (2019). Rh(III)-Catalyzed [5+2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT. Org. Lett. 21, 6, 1779-1783. [doi: 10.1021/acs.orglett.9b00354]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstractA novel and mild Rh(III)-catalyzed [5+2] oxidative annulation between cyclic arylguanidines and alkynes efficiently affords 1,3-benzodiazepines (pentacyclic guanidines). The use of O2 as the sole oxidant in place commonly used metal oxidants such as AgOAc clearly improves the efficiency of the oxidative annulation process. The mechanism of the cycloaddition most likely involves the formation of an eight-membered rhodacycle. DFT calculations support a striking mechanistic proposal for the [5+2] oxidative annulation.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from MINECO (projects CTQ2014-59015R, CTQ2017-87939R and ORFEO-CINQA network CTQ2016-81797-REDC), the Xunta de Galicia (project GRC2014/032, ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2016–2019, ED431G/09) and the European Union (European Regional Development Fund - ERDF). N. M.-Y. thanks MINECO and Xunta de Galicia for a predoctoral contractgl
dc.identifier.citationMartínez-Yáñez, N., Suárez, J., Cajaraville, A., Varela, J. A., Saá, C. (2019). Rh(III)-Catalyzed [5+2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFT. Org. Lett. 21, 6, 1779-1783gl
dc.identifier.doi10.1021/acs.orglett.9b00354
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/23354
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.9b00354gl
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.subjectArylguanidinesgl
dc.subject1,3-Benzodiazepinesgl
dc.subjectOxidative Annulationgl
dc.subjectRhodiumgl
dc.titleRh(III)-Catalyzed [5+2] Oxidative Annulation of Cyclic Arylguanidines and Alkynes to 1,3-Benzodiazepines. A Striking Mechanistic Proposal from DFTgl
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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