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Filling the Gaps in the Challenging AsymmetricHydroboration of 1,1-Disubstituted Alkenes with Simple Phosphite-Based Phosphinooxazoline Iridium Catalysts

  • Dades identificatives

    Identificador: PC:1257
    Autors:
    Montserrat DiéguezMaria BioscaMarc MagreOscar Pàmies
    Resum:
    We have identified a readily accessible phosphinooxazoline based phosphite-oxazoline catalytic system, (S)-4-isopropyl-2-{2-[(3,3¿,5,5¿-tetra-tert-butyl-1,1¿-biphenyl-2,2¿-diyl)phosphite]-phenyl}-2-oxazoline (L1 a), that can hydroborate a range of 1,1-disubstituted aryl olefins with high enantioselectivity (up to 94%), excellent yields and perfect regioselectivity. The new phosphite-oxazoline ligands efficiently hydroborate a broader range of olefins than previous phosphinooxazoline ligands. In particular, a wide range of a-tert-butylstyrenes can be hydroborated that bear aryl substituents with different electronic and steric properties, which complements previous results with N-heterocyclic copper catalysts, the only other system reported to date that has achieved these reactions.
  • Altres:

    Autor segons l'article: Montserrat Diéguez Maria Biosca Marc Magre Oscar Pàmies
    Departament: Química Física i Inorgànica
    Autor/s de la URV: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Maria Biosca Marc Magre PAMIES OLLÉ, OSCAR
    Paraules clau: asymmetric catalysis
    Resum: We have identified a readily accessible phosphinooxazoline based phosphite-oxazoline catalytic system, (S)-4-isopropyl-2-{2-[(3,3¿,5,5¿-tetra-tert-butyl-1,1¿-biphenyl-2,2¿-diyl)phosphite]-phenyl}-2-oxazoline (L1 a), that can hydroborate a range of 1,1-disubstituted aryl olefins with high enantioselectivity (up to 94%), excellent yields and perfect regioselectivity. The new phosphite-oxazoline ligands efficiently hydroborate a broader range of olefins than previous phosphinooxazoline ligands. In particular, a wide range of a-tert-butylstyrenes can be hydroborated that bear aryl substituents with different electronic and steric properties, which complements previous results with N-heterocyclic copper catalysts, the only other system reported to date that has achieved these reactions.
    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: 1867-3880
    Identificador de l'autor: 0000-0002-8450-0656 n/a n/a 0000-0002-2352-8508
    Data d'alta del registre: 2015-11-26
    Pàgina final: 120
    Volum de revista: 7
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cctc.201402822
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1002/cctc.201402822
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2014
    Pàgina inicial: 114
    Tipus de publicació: Post-print
  • Paraules clau:

    Catàlisi asimètrica
    asymmetric catalysis
    Chemistry
    Química
    Química
    1867-3880
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