Copper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Salts

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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.authorPérez Saavedra, Borja
dc.contributor.authorVázquez Galiñanes, Nuria
dc.contributor.authorSaá, Carlos
dc.contributor.authorFañanás-Mastral, Martín
dc.date.accessioned2018-07-06T13:20:54Z
dc.date.available2018-08-02T01:00:08Z
dc.date.issued2017-08-02
dc.description.abstractA copper-catalyzed tandem carboarylation/cyclization of alkynyl phosphonates with diaryliodonium salts is reported. The reaction gives straightforward access to valuable cyclic enol phosphonates in good yields under mild conditions. This transformation entails an initial chemoselective arylation of the alkyne followed by an intramolecular trapping of an intermediate vinyl cation by the phosphoryl group. Observation of β-aryl rearrangements across the double bond in intermediates generated from 1,2-diaryl alkynes support the intermediacy of a vinyl cation.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipFinancial support from MINECO (RYC-2012-11749; CTQ2015-62724-ERC; CTQ2014-59015-R), Xunta de Galicia (ED431F 2016/006; GRC2014/032; Centro singular de investigación de Galicia accreditation 2016-2019, ED431G/09) and the European Regional Development Fund (ERDF) is gratefully acknowledged. We also thank the ORFEO−CINQA network (CTQ2014-51912REDC). M. F.-M. is grateful to MINECO for a Ramón y Cajal contract. B.P.-S. thanks Xunta de Galicia for a predoctoral fellowshipgl
dc.identifier.citationBorja Pérez-Saavedra, Nuria Vázquez-Galiñanes, Carlos Saá, and Martín Fañanás-Mastral ACS Catalysis 2017 7 (9), 6104-6109 DOI: 10.1021/acscatal.7b02434gl
dc.identifier.doi10.1021/acscatal.7b02434
dc.identifier.essn2155-5435
dc.identifier.urihttp://hdl.handle.net/10347/16980
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/CTQ2014-51912/ES/RED ORFEO-CINQA "CENTRO DE INNOVACION EN QUIMICA AVANZADA”
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-62724-ERC/ES/FUNCIONALIZACION DE METANO A TRAVES DE CATALISIS COOPERATIVA EN PROCESOS DE ACTIVACION C-H Y FORMACION DE ENLACES C-C
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-59015-R/ES/SINTESIS SOSTENIBLE DE FARMACOFOROS HETEROCICLICOS Y GRAFENOS BIFENILENICOS MEDIANTE TRANSFORMACIONES CATALITICAS ORGANOMETALICAS
dc.relation.publisherversionhttps://doi.org/10.1021/acscatal.7b02434gl
dc.rights© 2017 American Chemical Societygl
dc.rights.accessRightsopen accessgl
dc.subjectAlkynesgl
dc.subjectCarbocationsgl
dc.subjectCoppergl
dc.subjectDiaryliodonium saltsgl
dc.subjectPhosphonatesgl
dc.titleCopper(I)-Catalyzed Tandem Carboarylation/Cyclization of Alkynyl Phosphonates with Diaryliodonium Saltsgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
relation.isAuthorOfPublication9dca33cc-3c8d-4d1c-8644-76987c972089
relation.isAuthorOfPublication.latestForDiscovery9dca33cc-3c8d-4d1c-8644-76987c972089

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