Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles

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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.authorBernárdez Alfaya, Rodrigo
dc.contributor.authorSuárez Rivero, Jaime
dc.contributor.authorFañanás-Mastral, Martín
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2020-10-05T06:56:04Z
dc.date.available2020-10-05T06:56:04Z
dc.date.issued2016
dc.descriptionThis is the peer reviewed version of the following article: Bernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocycles. Org. Lett., 18, 4, 642-645. [doi: 10.1021/acs.orglett.5b03499]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving.gl
dc.description.abstractA novel route to 1,3-oxazaheterocycles based on cooperative Ru–H/Brønsted acid catalysis is reported. The use of the commercially available RuH2(CO)(PPh3)3 complex allows for an efficient long distance chain-walking process while the Brønsted acid is responsible for generation of an electrophilic iminium ion which is trapped intramolecularly by an alcohol moiety. The alcohol, besides its nucleophilic function, also plays an important role in the stabilization of the Ru catalyst.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work was supported by MINECO (Spain) (projects CTQ2011-28258 and CTQ2014-59015R), Xunta de Galicia (project GRC2014/032) and the European Regional Development Fund (projects CTQ2014-59015R and GRC2014/032). R. B. thanks MEC for a predoctoral FPU fellowship and J. S. thanks XUGA for a postdoctoral contract. M. F.-M. thanks MINECO for a "Ramón y Cajal" contractgl
dc.identifier.citationBernárdez, R., Suárez, J., Fañanás-Mastral, M., Varela, J. A., Saá, C. (2016). Tandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxa-zaheterocycles. Org. Lett., 18, 4, 642-645gl
dc.identifier.doi10.1021/acs.orglett.5b03499
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/23351
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/MICINN/Plan Nacional de I+D+i 2008-2011/CTQ2011-28258/ES/CATALISIS ORGANOMETALICA: FUNCIONALIZACION DE ENLACES C-H
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.5b03499gl
dc.rightsCopyright © 2016 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving.gl
dc.rights.accessRightsopen accessgl
dc.subjectHydrocarbonsgl
dc.subjectReactions productsgl
dc.subjectCatalysisgl
dc.subjectIsomerizationgl
dc.subjectBrönsted-acidgl
dc.subjectChain walkinggl
dc.subjectRutheniumgl
dc.titleTandem Long Distance Chain-Walking/Cyclization via RuH2(CO)(PPh3)3/Brønsted Acid Catalysis: Entry to Aromatic Oxazaheterocyclesgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
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relation.isAuthorOfPublicatione9be05f9-b5a3-405c-aaf6-4e32700dd21d
relation.isAuthorOfPublication2c024eb2-7698-4785-bd0c-518f70068330
relation.isAuthorOfPublication.latestForDiscovery9dca33cc-3c8d-4d1c-8644-76987c972089

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