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A Theoretically-Guided Optimization of a New Family of Modular P,S-Ligands for Iridium-Catalyzed Hydrogenation of Minimally Functionalized Olefins

  • Datos identificativos

    Identificador: PC:1258
    Autores:
    Miquel A. PericàsMontserrat DiéguezJavier MazuelaMercè CollErik A. KarlssonXisco CaldenteyJèssica MargalefOscar Pàmies
    Resumen:
    A library of modular iridium complexes derived from thioether-phosphite/phosphinite ligands has been evaluated in the asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins. The modular ligand design has been shown to be crucial in finding highly selective catalysts for each substrate. A DFT study of the transition state responsible for the enantiocontrol in the Ir-catalyzed hydrogenation is also described and used for further optimization of the crucial stereodefining moieties. Excellent enantioselectivities (enantiomeric excess (ee) values up to 99%) have been obtained for a range of substrates, including E- and Ztrisubstituted and disubstituted olefins, a,b-unsaturated enones, tri- and disubstituted alkenylboronic esters, and olefins with trifluoromethyl substituents.
  • Otros:

    Autor según el artículo: Miquel A. Pericàs Montserrat Diéguez Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef Oscar Pàmies
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: Miquel A. Pericàs DIÉGUEZ FERNÁNDEZ, MONTSERRAT Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef PAMIES OLLÉ, OSCAR
    Palabras clave: Asymmetric catalysis
    Resumen: A library of modular iridium complexes derived from thioether-phosphite/phosphinite ligands has been evaluated in the asymmetric iridium-catalyzed hydrogenation of minimally functionalized olefins. The modular ligand design has been shown to be crucial in finding highly selective catalysts for each substrate. A DFT study of the transition state responsible for the enantiocontrol in the Ir-catalyzed hydrogenation is also described and used for further optimization of the crucial stereodefining moieties. Excellent enantioselectivities (enantiomeric excess (ee) values up to 99%) have been obtained for a range of substrates, including E- and Ztrisubstituted and disubstituted olefins, a,b-unsaturated enones, tri- and disubstituted alkenylboronic esters, and olefins with trifluoromethyl substituents.
    Grupo de investigación: Organometàl.lics i Catàlisi Homogènia
    Áreas temáticas: Chemistry Química Química
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0947-6539
    Identificador del autor: 0000-0003-0195-8846 0000-0002-8450-0656 n/a n/a n/a n/a n/a 0000-0002-2352-8508
    Fecha de alta del registro: 2015-11-26
    Página final: 21214
    Volumen de revista: 20
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201402978
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1002/chem.201402978
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2014
    Página inicial: 21201
    Tipo de publicación: Post-print
  • Palabras clave:

    Catàlisi asimètrica
    Asymmetric catalysis
    Chemistry
    Química
    Química
    0947-6539
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