Articles producció científica> Química Física i Inorgànica

Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions

  • Identification data

    Identifier: imarina:4123832
    Handle: http://hdl.handle.net/20.500.11797/imarina4123832
  • Authors:

    Biosca M
    Margalef J
    Caldentey X
    Besora M
    Rodríguez-Escrich C
    Saltó J
    Cambeiro X
    Maseras F
    Pàmies O
    Diéguez M
    Pericàs M
  • Others:

    Author, as appears in the article.: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M
    Department: Química Física i Inorgànica
    URV's Author/s: Besora Bonet, Maria / Biosca Brull, Maria / Diéguez Fernández, Montserrat / Pamies Ollé, Oscar
    Keywords: Hashtag Etiqueta «#» @uroweb @residentesaeu @infoAeu
    Abstract: © 2018 American Chemical Society. A modular approach employing indene as common starting material, has enabled the straightforward preparation in three reaction steps of P-thioether ligands for the Pd-catalyzed asymmetric allylic substitution. The analysis of a starting library of P-thioether ligands based on rational design and theoretical calculations has led to the discovery of an optimized anthracenethiol derivative with excellent behavior in the reaction of choice. Improving most approaches reported to date, this ligand presents a broad substrate and nucleophile scope. Excellent enantioselectivities have been achieved for a range of linear and cyclic allylic substrates using a large number of C-, N-, and O-nucleophiles (40 compounds in total). The species responsible for the catalytic activity have been further investigated by NMR in order to clearly establish the origin of the enantioselectivity. The resulting products have been derivatized by means of ring-closing metathesis or Pauson-Khand reactions to further prove the synthetic versatility of the methodology for preparing enantiopure complex structures.
    Thematic Areas: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 21555435
    Author's mail: maria.besora@urv.cat maria.biosca@urv.cat montserrat.dieguez@urv.cat oscar.pamies@urv.cat
    Author identifier: 0000-0002-6656-5827 0000-0002-9116-6318 0000-0002-8450-0656 0000-0002-2352-8508
    Last page: 3601
    Record's date: 2023-02-22
    Journal volume: 8
    Papper version: info:eu-repo/semantics/submittedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/acscatal.7b04192
    Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Acs Catalysis. 8 (4): 3587-3601
    APA: Biosca M; Margalef J; Caldentey X; Besora M; Rodríguez-Escrich C; Saltó J; Cambeiro X; Maseras F; Pàmies O; Diéguez M; Pericàs M (2018). Computationally guided design of a readily assembled phosphite-thioether ligand for a broad range of pd-catalyzed asymmetric allylic substitutions. Acs Catalysis, 8(4), 3587-3601. DOI: 10.1021/acscatal.7b04192
    Article's DOI: 10.1021/acscatal.7b04192
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2018
    First page: 3587
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry (Miscellaneous),Chemistry, Physical
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Engenharias ii
    Ciências agrárias i
    Chemistry, physical
    Chemistry (miscellaneous)
    Chemistry (all)
    Catalysis
    Astronomia / física
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