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    Deconstructing selectivity in the gold-promoted cyclization of alkynyl benzothioamides to six-membered mesoionic carbene or acyclic carbene complexes

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    Type
    Article
    Authors
    Vummaleti, Sai V. C. cc
    Falivene, Laura cc
    Poater, Albert cc
    Cavallo, Luigi cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2014-03-27
    Online Publication Date
    2014-03-27
    Print Publication Date
    2014-05-02
    Permanent link to this record
    http://hdl.handle.net/10754/563538
    
    Metadata
    Show full item record
    Abstract
    We demonstrate that the experimentally observed switch in selectivity from 5-exo-dig to 6-endo-dig cyclization of an alkynyl substrate, promoted by Au I and AuIII complexes, is connected to a switch from thermodynamic to kinetic reaction control. The AuIII center pushes alkyne coordination toward a single Au-C(alkyne) σ-bond, conferring carbocationic character (and reactivity) to the distal alkyne C atom. © 2014 American Chemical Society.
    Citation
    Vummaleti, S. V. C., Falivene, L., Poater, A., & Cavallo, L. (2014). Deconstructing Selectivity in the Gold-Promoted Cyclization of Alkynyl Benzothioamides to Six-Membered Mesoionic Carbene or Acyclic Carbene Complexes. ACS Catalysis, 4(5), 1287–1291. doi:10.1021/cs5001575
    Publisher
    American Chemical Society (ACS)
    Journal
    ACS Catalysis
    DOI
    10.1021/cs5001575
    ae974a485f413a2113503eed53cd6c53
    10.1021/cs5001575
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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