Articles producció científica> Química Física i Inorgànica

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

  • Identification data

    Identifier: PC:1257
    Authors:
    Montserrat DiéguezMaria BioscaMarc MagreOscar Pàmies
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Montserrat Diéguez Maria Biosca Marc Magre Oscar Pàmies
    Department: Química Física i Inorgànica
    URV's Author/s: DIÉGUEZ FERNÁNDEZ, MONTSERRAT Maria Biosca Marc Magre PAMIES OLLÉ, OSCAR
    Keywords: asymmetric catalysis
    Abstract: 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.
    Research group: Organometàl.lics i Catàlisi Homogènia
    Thematic Areas: Chemistry Química Química
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 1867-3880
    Author identifier: 0000-0002-8450-0656 n/a n/a 0000-0002-2352-8508
    Record's date: 2015-11-26
    Last page: 120
    Journal volume: 7
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cctc.201402822
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/cctc.201402822
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2014
    First page: 114
    Publication Type: Post-print
  • Keywords:

    Catàlisi asimètrica
    asymmetric catalysis
    Chemistry
    Química
    Química
    1867-3880
  • Documents:

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