Articles producció científica> Química Física i Inorgànica

Extending the Substrate Scope of Bicyclic P-Oxazoline/Thiazole Ligands for Ir-Catalyzed Hydrogenation of Unfunctionalized Olefins by Introducing a Biaryl Phosphoroamidite Group

  • Identification data

    Identifier: PC:1254
    Authors:
    Montserrat DiéguezPher G. AnderssonAlexander PaptchkhineMaria BioscaOscar Pàmies
    Abstract:
    This study identifies a series of Ir-bicyclic phosphoroamidite–oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and a,b-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite–oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane–oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite–oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N- phosphane–oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.
  • Others:

    Author, as appears in the article.: Montserrat Diéguez Pher G. Andersson Alexander Paptchkhine Maria Biosca Oscar Pàmies
    Department: Química Física i Inorgànica
    URV's Author/s: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Pher G. Andersson Alexander Paptchkhine Maria Biosca PAMIES OLLÉ, OSCAR
    Keywords: Asymmetric catalysis Hydrogenation
    Abstract: This study identifies a series of Ir-bicyclic phosphoroamidite–oxazoline/thiazole catalytic systems that can hydrogenate a wide range of minimally functionalized olefins (including E- and Z-tri- and disubstituted substrates, vinylsilanes, enol phosphinates, tri- and disubstituted alkenylboronic esters, and a,b-unsaturated enones) in high enantioselectivities (ee values up to 99%) and conversions. The design of the new phosphoroamidite–oxazoline/thiazole ligands derives from a previous successful generation of bicyclic N-phosphane–oxazoline/thiazole ligands, by replacing the N-phosphane group with a p-acceptor biaryl phosphoroamidite moiety. A small but structurally important family of Ir-phosphoroamidite–oxazoline/thiazole precatalysts has thus been synthesized by changing the nature of the Ndonor group (either oxazoline or thiazole) and the configuration at the biaryl phosphoroamidite moiety. The substitution of the N-phosphane by a phosphoroamidite group in the bicyclic N- phosphane–oxazoline/thiazole ligands extended the range of olefins that can be successfully hydrogenated.
    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: 0000-0002-8450-0656 n/a n/a n/a 0000-0002-2352-8508
    Record's date: 2015-10-30
    Last page: 3464
    Journal volume: 21
    Papper version: info:eu-repo/semantics/submittedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201405361
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/chem.201405361
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2015
    First page: 3455
    Publication Type: Pre-print
  • Keywords:

    Hidrogenació
    Catàlisi asimètrica
    Asymmetric catalysis
    Hydrogenation
    Chemistry
    Química
    Química
    0947-6539
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