Pd-Catalyzed (3 + 2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans

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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.authorVerdugo Leal, Felipe Ignacio
dc.contributor.authorConcepción Vicente, Eduardo da
dc.contributor.authorRodiño Balboa, Ricardo
dc.contributor.authorCalvelo Souto, Martín
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorLópez García, Fernando
dc.date.accessioned2020-07-24T11:57:09Z
dc.date.available2021-06-12T01:00:07Z
dc.date.issued2020
dc.descriptionThis document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acscatal.0c01827gl
dc.description.abstractA Pd catalyst made from a Pd(0) source and a bulky biaryl phosphine ligand promotes highly efficient intramolecular (3 + 2) heterocycloadditions between alkylidenecyclopropanes (ACPs) and carbonyls. The annulations provide a straightforward access to fused polycyclic systems featuring β-methylene tetrahydrofuran moieties. DFT data support a pallada–ene process and shed light on the critical role of hemilabile interactions between the Pd center and the bulky biaryl phosphine. Significantly, these Pd(0) catalysts are also effective for promoting intermolecular formal cycloadditions between ACPs and trifluoromethyl ketones, thus providing for a direct entry to chiral tetrahydrofuran moieties (THFs) bearing trifluoromethyl–substituted carbonsgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work received financial support from the Spanish MINECO (SAF2016-76689-R, CTQ2017-84767-P), the Xunta de Galicia (ED431C 2017/19, 2015-CP082, Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03, and a predoctoral Fellowship to E.d.C. and M.C.), CONICYT (grant to F.V.), and the ERDF, ERC (Adv. Grant 340055). The Orfeo–Cinqa network (CTQ2016-81797-REDC) is also acknowledgedgl
dc.identifier.citationACS Catal. 2020, 10, 14, 7710–7718gl
dc.identifier.doi10.1021/acscatal.0c01827
dc.identifier.essn2155-5435
dc.identifier.urihttp://hdl.handle.net/10347/23209
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/FP7/340055
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/SAF2016-76689-R/ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-84767-P/ES/METODOS SINTETICOS EFICIENTES BASADOS EN CATALISIS METALICA. DESARROLLOS ENANTIOSELECTIVOS Y ACCESO A MOLECULAS BIOACTIVAS Y/O DE ALTO INTERES SINTETICO
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/acscatal.0c01827gl
dc.rights© 2020 American Chemical Society. This article may be used for non-commercial purposes in accordance with ACS Terms and Conditions for Use of Self-Archived Versionsgl
dc.rights.accessRightsopen accessgl
dc.subjectPalladiumgl
dc.subjectHydrocarbonsgl
dc.subjectCyclizationgl
dc.subjectKetonesgl
dc.subjectCatalystsgl
dc.subjectAlkylidenecyclopropanegl
dc.subjectCycloadditiongl
dc.titlePd-Catalyzed (3 + 2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofuransgl
dc.typejournal articlegl
dc.type.hasVersionAMgl
dspace.entity.typePublication
relation.isAuthorOfPublicationdd645598-c57c-4276-88fd-6933845cb9b2
relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication.latestForDiscoverydd645598-c57c-4276-88fd-6933845cb9b2

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