Articles producció científica> Química Analítica i Química Orgànica

H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis

  • Identification data

    Identifier: imarina:9244735
  • Authors:

    Franchino A
    Martí À
    Echavarren AM
    Journal Of The American Chemical Society
    10.1021/jacs.1c11978
    Journal Of The American Chemical Society. 144 (8): 3497-3509
  • Others:

    Author, as appears in the article.: Franchino A; Martí À; Echavarren AM
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO / Martí Zaragoza, Àlex
    Keywords: Chiral bronsted acid transfer hydrogenation phosphoric-acid noncovalent interactions metal catalysis ligands hydroalkoxylation highly substituted furans gold complexes
    Abstract: A new strategy for enantioselective transition-metal catalysis is presented, wherein a H-bond donor placed on the ligand of a cationic complex allows precise positioning of the chiral counteranion responsible for asymmetric induction. The successful implementation of this paradigm is demonstrated in 5-exo-dig and 6-endo-dig cyclizations of 1,6-enynes, combining an achiral phosphinourea Au(I) chloride complex with a BINOL-derived phosphoramidate Ag(I) salt and thus allowing the first general use of chiral anions in Au(I)-catalyzed reactions of challenging alkyne substrates. Experiments with modified complexes and anions, 1H NMR titrations, kinetic data, and studies of solvent and nonlinear effects substantiate the key H-bonding interaction at the heart of the catalytic system. This conceptually novel approach, which lies at the intersection of metal catalysis, H-bond organocatalysis, and asymmetric counterion-directed catalysis, provides a blueprint for the development of supramolecularly assembled chiral ligands for metal complexes.
    Thematic Areas: Química Materiais Interdisciplinar General chemistry Farmacia Engenharias iv Engenharias iii Engenharias ii Colloid and surface chemistry Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biochemistry Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: antoniomaria.echavarren@urv.cat alex.marti@estudiants.urv.cat
    Author identifier: 0000-0002-6418-7930
    Record's date: 2024-07-20
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/jacs.1c11978
    Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Journal Of The American Chemical Society. 144 (8): 3497-3509
    APA: Franchino A; Martí À; Echavarren AM (2022). H-Bonded Counterion-Directed Enantioselective Au(I) Catalysis. Journal Of The American Chemical Society, 144(8), 3497-3509. DOI: 10.1021/jacs.1c11978
    Article's DOI: 10.1021/jacs.1c11978
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2022
    Publication Type: Journal Publications
  • Keywords:

    Biochemistry,Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Colloid and Surface Chemistry
    Chiral bronsted acid
    transfer hydrogenation
    phosphoric-acid
    noncovalent interactions
    metal catalysis
    ligands
    hydroalkoxylation
    highly substituted furans
    gold
    complexes
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Farmacia
    Engenharias iv
    Engenharias iii
    Engenharias ii
    Colloid and surface chemistry
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biochemistry
    Astronomia / física
  • Documents:

  • Cerca a google

    Search to google scholar