Chiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C–H Activation/Cycloaddition Reactions

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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.authorGonzález González, José Manuel
dc.contributor.authorVidal Pereira, Xandro
dc.contributor.authorOrtuño Maqueda, Manuel Ángel
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorGulías Costa, Moisés
dc.date.accessioned2022-12-30T12:50:53Z
dc.date.available2022-12-30T12:50:53Z
dc.date.issued2022
dc.description.abstractWe report the first examples of the use of a new class of ligands (NOBINAc) for performing asymmetric C–H activations using palladium catalysts. These ligands combine the axial chirality of binaphthyl scaffolds with the bifunctional and bidentate coordination properties of mono-N-protected amino acids (MPAAs), which are well-known to favor Pd-promoted C–H activations via concerted metalation–deprotonation mechanisms. We demonstrate that our new ligands enable substantially higher enantioselectivities than MPAAs in the assembly of 2-benzazepines through formal (5 + 2) cycloadditions between homobenzyltriflamides or o-methylbenzyltriflamides and allenesgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work received financial support from the MCIN/AEI/10.13039/501100011033 (Projects PID2019-108624RB-I00, PID2019-110385GB-I00, and PID2020-119116RA-I00 and FPU Fellowship to X.V.), the Consellería de Cultura, Educación e Ordenación Universitaria (ED431C-2021/25, ED431G 2019/03: Centro Singular de Investigación de Galicia accreditation 2019–2022, and fellowship to J.M.G.), and the European Regional Development Fund (ERDF). The orfeo-cinqa network CTQ2016-81797-REDC is also kindly acknowledged. M.A.O. acknowledges the Xunta Distinguished Researcher Program (ED431H 2020/21) for funding and Centro de Supercomputación de Galicia (CESGA) for providing generous computational resources. Figures were created with CYLview20gl
dc.identifier.citationJ. Am. Chem. Soc. 2022, 144, 47, 21437–21442gl
dc.identifier.doi10.1021/jacs.2c09479
dc.identifier.essn1520-5126
dc.identifier.issn0002-7863
dc.identifier.urihttp://hdl.handle.net/10347/29687
dc.language.isoenggl
dc.publisherACS Publicationsgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-108624RB-I00/ES/HERRAMIENTAS BASADAS EN METALES PARA SU USO EN QUIMICA BIOLOGICA Y BIOMEDICINA. DESARROLLO DE NUEVAS ESTRATEGIAS ANTICANCERgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110385GB-I00/NUEVOS METODOS DE SINTESIS QUIMICA MEDIANTE LA FUNCIONALIZACION DE ENLACES C-H CON CATALIZADORES METALICOSgl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/REDES METAL-ORGANICAS PARA LA VALORIZACION DE BIOMASA A TRAVES DE SIMULACIONES DE SISTEMAS CATALITICOS
dc.relation.publisherversionhttps://doi.org/10.1021/jacs.2c09479gl
dc.rights© 2022 The Authors. Published by American Chemical Society. This work is under a CC Attribution 4.0 International (CC BY 4.0)gl
dc.rightsAtribución 4.0 Internacional
dc.rights.accessRightsrestricted accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAllenesgl
dc.subjectAnnulationsgl
dc.subjectChemical structuregl
dc.subjectLigandsgl
dc.subjectStereoselectivitygl
dc.titleChiral Ligands Based on Binaphthyl Scaffolds for Pd-Catalyzed Enantioselective C–H Activation/Cycloaddition Reactionsgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
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relation.isAuthorOfPublication5ae222c9-f626-432b-aac5-da78c06ed64f
relation.isAuthorOfPublication47a6a088-27a9-412e-8422-0de4fd8af0d4
relation.isAuthorOfPublication.latestForDiscoveryca0cd81f-fe57-4eaf-9354-6a609625500e

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