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

  • Datos identificativos

    Identificador: PC:1254
    Autores:
    Montserrat DiéguezPher G. AnderssonAlexander PaptchkhineMaria BioscaOscar Pàmies
    Resumen:
    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.
  • Otros:

    Autor según el artículo: Montserrat Diéguez Pher G. Andersson Alexander Paptchkhine Maria Biosca Oscar Pàmies
    Departamento: Química Física i Inorgànica
    Autor/es de la URV: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Pher G. Andersson Alexander Paptchkhine Maria Biosca PAMIES OLLÉ, OSCAR
    Palabras clave: Asymmetric catalysis Hydrogenation
    Resumen: 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.
    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: 0000-0002-8450-0656 n/a n/a n/a 0000-0002-2352-8508
    Fecha de alta del registro: 2015-10-30
    Página final: 3464
    Volumen de revista: 21
    Versión del articulo depositado: info:eu-repo/semantics/submittedVersion
    Enlace a la fuente original: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201405361
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI del artículo: 10.1002/chem.201405361
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2015
    Página inicial: 3455
    Tipo de publicación: Pre-print
  • Palabras clave:

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