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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

  • Identification data

    Identifier: PC:1258
    Authors:
    Miquel A. PericàsMontserrat DiéguezJavier MazuelaMercè CollErik A. KarlssonXisco CaldenteyJèssica MargalefOscar Pàmies
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Miquel A. Pericàs Montserrat Diéguez Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef Oscar Pàmies
    Department: Química Física i Inorgànica
    URV's Author/s: Miquel A. Pericàs DIÉGUEZ FERNÁNDEZ, MONTSERRAT Javier Mazuela Mercè Coll Erik A. Karlsson Xisco Caldentey Jèssica Margalef PAMIES OLLÉ, OSCAR
    Keywords: Asymmetric catalysis
    Abstract: 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.
    Research group: Organometàl.lics i Catàlisi Homogènia
    Thematic Areas: Chemistry Química Química
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0947-6539
    Author identifier: 0000-0003-0195-8846 0000-0002-8450-0656 n/a n/a n/a n/a n/a 0000-0002-2352-8508
    Record's date: 2015-11-26
    Last page: 21214
    Journal volume: 20
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201402978
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/chem.201402978
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2014
    First page: 21201
    Publication Type: Post-print
  • Keywords:

    Catàlisi asimètrica
    Asymmetric catalysis
    Chemistry
    Química
    Química
    0947-6539
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