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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

  • Dades identificatives

    Identificador: PC:1258
    Autors:
    Miquel A. PericàsMontserrat DiéguezJavier MazuelaMercè CollErik A. KarlssonXisco CaldenteyJèssica MargalefOscar Pàmies
    Resum:
    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.
  • Altres:

    Autor segons l'article: Miquel A. Pericàs Montserrat Diéguez Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef Oscar Pàmies
    Departament: Química Física i Inorgànica
    Autor/s de la URV: Miquel A. Pericàs DIÉGUEZ FERNÁNDEZ, MONTSERRAT Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef PAMIES OLLÉ, OSCAR
    Paraules clau: Asymmetric catalysis
    Resum: 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.
    Grup de recerca: Organometàl.lics i Catàlisi Homogènia
    Àrees temàtiques: Chemistry Química Química
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0947-6539
    Identificador de l'autor: 0000-0003-0195-8846 0000-0002-8450-0656 n/a n/a n/a n/a n/a 0000-0002-2352-8508
    Data d'alta del registre: 2015-11-26
    Pàgina final: 21214
    Volum de revista: 20
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201402978
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1002/chem.201402978
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2014
    Pàgina inicial: 21201
    Tipus de publicació: Post-print
  • Paraules clau:

    Catàlisi asimètrica
    Asymmetric catalysis
    Chemistry
    Química
    Química
    0947-6539
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