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Regioirregular and catalytic Mizoroki-Heck reactions

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Regioirregular and catalytic Mizoroki-Heck reactions

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dc.contributor.author Garnes-Portoles, Francisco es_ES
dc.contributor.author Greco, Rossella es_ES
dc.contributor.author Oliver-Meseguer, Judit es_ES
dc.contributor.author Castellanos-Soriano, Jorge es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Lopez-Haro, Miguel es_ES
dc.contributor.author Hernández-Garrido, Juan Carlos es_ES
dc.contributor.author Boronat Zaragoza, Mercedes es_ES
dc.contributor.author Pérez-Ruiz, Raúl es_ES
dc.contributor.author Leyva Perez, Antonio es_ES
dc.date.accessioned 2022-09-13T18:02:58Z
dc.date.available 2022-09-13T18:02:58Z
dc.date.issued 2021-04 es_ES
dc.identifier.uri http://hdl.handle.net/10251/185960
dc.description.abstract [EN] The palladium-catalysed cross-coupling reaction between alkenes and aryl halides (the Mizoroki-Heck reaction) is a powerful methodology to construct new carbon-carbon bonds. However, the success of this reaction is in part hampered by an extremely marked regioselectivity on the double bond, which dictates that electron-poor alkenes react exclusively on the beta-carbon. Here, we show that ligand-free, few-atom palladium clusters in solution catalyse the alpha-selective intramolecular Mizoroki-Heck coupling of iodoaryl cinnamates, and mechanistic studies support the formation of a sterically encumbered cinnamate-palladium cluster intermediate. Following this rationale, the alpha-selective intermolecular coupling of aryl iodides with styrenes is also achieved with palladium clusters encapsulated within fine-tuned and sterically restricted zeolite cavities to produce 1,1-bisarylethylenes, which are further engaged with aryl halides by a metal-free photoredox-catalysed coupling. These ligand-free methodologies significantly expand the chemical space of the Mizoroki-Heck coupling. es_ES
dc.description.sponsorship This work was supported by MINECO (Spain, projects CTQ 2017-86735-P, PID2019-105391GB-C22 and MAT2017-82288-C2-1-P, Severo Ochoa programme SEV-2016-0683 and the Juan de la Cierva programme). F.G.-P. and R.G. thank ITQ for the concession of a contract. J.O.-M. acknowledges the Juan de la Cierva programme for the concession of a contract, and R.P.-R. and J.C.-S. thank the Plan GenT programme (CIDEGENT/2018/044) funded by Generalitat Valenciana. HR STEM measurements were performed at DME-UCA in Cadiz University, with financial support from FEDER/MINECO (PID2019-110018GA-I00 and PID2019-107578GA-I00). We acknowledge ALBA Synchrotron for allocating beamtime and CL AE SS beamline staff for their technical support during our experiment. es_ES
dc.language Inglés es_ES
dc.publisher Nature Publishing Group es_ES
dc.relation.ispartof Nature Catalysis es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Regioirregular and catalytic Mizoroki-Heck reactions es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1038/s41929-021-00592-3 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//SEV-2016-0683/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-86735-P/ES/CATALISIS CON ATOMOS METALICOS AISLADOS Y CLUSTERES ULTRAPEQUEÑOS BIEN DEFINIDOS, SIN LIGANDOS Y CONFINADOS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GENERALITAT VALENCIANA//CIDEGENT%2F2018%2F044//AYUDA CIDEGENT CONTRATACION RAUL PEREZ RUIZ/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/MAT2017-82288-C2-1-P/ES/MATERIALES HIBRIDOS MULTIFUNCIONALES BASADOS EN NANO-UNIDADES ESTRUCTURALES ACTIVAS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-105391GB-C22/ES/DESARROLLO DE NUEVOS SISTEMAS DE CONVERSION BIFOTONICA A MAYOR FRECUENCIA BASADOS EN ANIQUILACION TRIPLETE-TRIPLETE PARA FOTOCATALISIS REDOX CON LUZ VISIBLE/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GENERALITAT VALENCIANA//CIDEGENT%2F2018%2F044//PHOTON UPCONVERSION REDOX CATALYSIS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107578GA-I00/ES/COMBINACION DE PLASMONICA Y CATALISIS PARA EL DESARROLLO DE NANOESTRUCTURAS BASADAS EN MOS2 PARA APLICACIONES DE ENERGIA LIMPIA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110018GA-I00/ES/HACIA CATALIZADORES HOMO Y HETERO DIATOMICOS DE AU-PD SOPORTADOS SOBRE OXIDOS: SINTEIS, CATACTERIZACION ATOMICA Y ACTIVIDAD EN LA REACCION DE OXIDACION SELECTIVA DE ALCOHOLES/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Garnes-Portoles, F.; Greco, R.; Oliver-Meseguer, J.; Castellanos-Soriano, J.; Jiménez Molero, MC.; Lopez-Haro, M.; Hernández-Garrido, JC.... (2021). Regioirregular and catalytic Mizoroki-Heck reactions. Nature Catalysis. 4(4):293-303. https://doi.org/10.1038/s41929-021-00592-3 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1038/s41929-021-00592-3 es_ES
dc.description.upvformatpinicio 293 es_ES
dc.description.upvformatpfin 303 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 4 es_ES
dc.description.issue 4 es_ES
dc.identifier.eissn 2520-1158 es_ES
dc.relation.pasarela S\437882 es_ES
dc.contributor.funder GENERALITAT VALENCIANA es_ES
dc.contributor.funder AGENCIA ESTATAL DE INVESTIGACION es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder Ministerio Ciencia, Innovación y Universidades es_ES
dc.contributor.funder MINISTERIO DE CIENCIA, INNOVACIÓN Y UNIVERSIDADES es_ES
dc.contributor.funder Ministerio de Economía, Industria y Competitividad es_ES
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