Articles producció científica> Química Analítica i Química Orgànica

Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, C-H Insertion, and Dimerization Reactions

  • Identification data

    Identifier: imarina:5873709
    Authors:
    García-Morales C, Pei XL, Sarria Toro JM, Echavarren AM
    Abstract:
    Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3 . The aryl carbenes react with PPh3 and alkenes to give stable phosphonium ylides and cyclopropanes, respectively. Oxidation with pyridine N-oxide and intermolecular C-H insertion to cyclohexane have also been observed. In the absence of nucleophiles, a bimolecular reaction, similar to that observed for other metal carbenes, leads to a symmetrical alkene.© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Others:

    Author, as appears in the article.: García-Morales C, Pei XL, Sarria Toro JM, Echavarren AM
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO
    Keywords: Structure elucidation Retro-buchner reaction Reactivity Mechanism Gold Generation Density-functional calculations Decomposition Complexes Cis Catalysis Carbenoids Carbenes Access
    Abstract: Mesityl gold(I) carbenes lacking heteroatom stabilization or shielding ancillary ligands have been generated and spectroscopically characterized from chloro(mesityl)methylgold(I) carbenoids bearing JohnPhos-type ligands by chloride abstraction with GaCl3 . The aryl carbenes react with PPh3 and alkenes to give stable phosphonium ylides and cyclopropanes, respectively. Oxidation with pyridine N-oxide and intermolecular C-H insertion to cyclohexane have also been observed. In the absence of nucleophiles, a bimolecular reaction, similar to that observed for other metal carbenes, leads to a symmetrical alkene.© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Thematic Areas: Química Medicina ii Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 14337851
    Author's mail: antoniomaria.echavarren@urv.cat
    Author identifier: 0000-0002-6418-7930
    Record's date: 2022-07-23
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201814577
    Papper original source: Angewandte Chemie (International Ed. Print). 58 (12): 3957-3961
    APA: García-Morales C, Pei XL, Sarria Toro JM, Echavarren AM (2019). Direct Observation of Aryl Gold(I) Carbenes that Undergo Cyclopropanation, C-H Insertion, and Dimerization Reactions. Angewandte Chemie (International Ed. Print), 58(12), 3957-3961. DOI: 10.1002/anie.201814577
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1002/anie.201814577
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2019
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Structure elucidation
    Retro-buchner reaction
    Reactivity
    Mechanism
    Gold
    Generation
    Density-functional calculations
    Decomposition
    Complexes
    Cis
    Catalysis
    Carbenoids
    Carbenes
    Access
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Astronomia / física
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