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New-Generation Ligand Design for the Gold-Catalyzed Asymmetric Activation of Alkynes

  • Identification data

    Identifier: imarina:9228610
    Authors:
    Zuccarello GEscofet ICaniparoli UEchavarren AM
    Abstract:
    Gold(I) catalysts are ideal for the activation of alkynes under very mild conditions. However, unlike allenes or alkenes, the triple bond of alkynes cannot be prochiral. In addition, the linear coordination displayed by gold(I) complexes places the chiral ligand far away from the substrate resulting in an inefficient transfer of chiral information. This poses a significant challenge for the achievement of high enantiocontrol in gold(I)-catalyzed reactions of alkynes. Although considerable progress on enantioselective gold(I)-catalyzed transformations has recently been achieved, the asymmetric activation of non-prochiral alkyne-containing small molecules still represents a great challenge. Herein we summarize recent advances in intra- and intermolecular enantioselective gold(I)-catalyzed reactions involving alkynes, discussing new chiral ligand designs that lie at the basis of these developments. We also focus on the mode of action of these catalysts, their possible limitations towards a next-generation of more efficient ligand designs. Finally, square planar chiral gold(III) complexes, which offer an alternative to chiral gold(I) complexes, are also discussed.
  • Others:

    Author, as appears in the article.: Zuccarello G; Escofet I; Caniparoli U; Echavarren AM
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO
    Keywords: Intermolecular 2+2 cycloaddition Gold Cyclization Chiral ligands Asymmetric catalysis Alkynes scalable synthesis phosphine-phosphite-ligands metal-complexes kinetic resolution homogeneous catalysis gold(iii) compounds gold enantioselective synthesis cyclobutane derivatives cyclization complexes synthesis chiral ligands asymmetric catalysis
    Abstract: Gold(I) catalysts are ideal for the activation of alkynes under very mild conditions. However, unlike allenes or alkenes, the triple bond of alkynes cannot be prochiral. In addition, the linear coordination displayed by gold(I) complexes places the chiral ligand far away from the substrate resulting in an inefficient transfer of chiral information. This poses a significant challenge for the achievement of high enantiocontrol in gold(I)-catalyzed reactions of alkynes. Although considerable progress on enantioselective gold(I)-catalyzed transformations has recently been achieved, the asymmetric activation of non-prochiral alkyne-containing small molecules still represents a great challenge. Herein we summarize recent advances in intra- and intermolecular enantioselective gold(I)-catalyzed reactions involving alkynes, discussing new chiral ligand designs that lie at the basis of these developments. We also focus on the mode of action of these catalysts, their possible limitations towards a next-generation of more efficient ligand designs. Finally, square planar chiral gold(III) complexes, which offer an alternative to chiral gold(I) complexes, are also discussed.
    Thematic Areas: Química General chemistry Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all)
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: antoniomaria.echavarren@urv.cat
    Author identifier: 0000-0002-6418-7930
    Record's date: 2024-07-27
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cplu.202100232
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Chempluschem. 86 (9): 1283-1296
    APA: Zuccarello G; Escofet I; Caniparoli U; Echavarren AM (2021). New-Generation Ligand Design for the Gold-Catalyzed Asymmetric Activation of Alkynes. Chempluschem, 86(9), 1283-1296. DOI: 10.1002/cplu.202100232
    Article's DOI: 10.1002/cplu.202100232
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2021
    Publication Type: Journal Publications
  • Keywords:

    Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Intermolecular 2+2 cycloaddition
    Gold
    Cyclization
    Chiral ligands
    Asymmetric catalysis
    Alkynes
    scalable synthesis
    phosphine-phosphite-ligands
    metal-complexes
    kinetic resolution
    homogeneous catalysis
    gold(iii) compounds
    gold
    enantioselective synthesis
    cyclobutane derivatives
    cyclization
    complexes synthesis
    chiral ligands
    asymmetric catalysis
    Química
    General chemistry
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
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