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    Mechanism of Intramolecular Rhodium- and Palladium-Catalyzed Alkene Alkoxyfunctionalizations

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    Type
    Article
    Authors
    Vummaleti, Sai V. C. cc
    Alghamdi, Miasser cc
    Poater, Albert cc
    Falivene, Laura cc
    Scaranto, Jessica
    Beetstra, Dirk J.
    Morton, Jason G.
    Cavallo, Luigi cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    SABIC - Corporate Research and Innovation Center (CRI) at KAUST
    Date
    2015-11-13
    Online Publication Date
    2015-11-13
    Print Publication Date
    2015-12-14
    Permanent link to this record
    http://hdl.handle.net/10754/621702
    
    Metadata
    Show full item record
    Abstract
    Density functional theory calculations have been used to investigate the reaction mechanism for the [Rh]-catalyzed intramolecular alkoxyacylation ([Rh] = [RhI(dppp)+] (dppp, 1,3-bis(diphenylphosphino)propane) and [Pd]/BPh3 dual catalytic system assisted intramolecular alkoxycyanation ([Pd] = Pd-Xantphos) using acylated and cyanated 2-allylphenol derivatives as substrates, respectively. Our results substantially confirm the proposed mechanism for both [Rh]- and [Pd]/ BPh3-mediated alkoxyfunctionalizations, offering a detailed geometrical and energetical understanding of all the elementary steps. Furthermore, for the [Rh]-mediated alkoxyacylation, our observations support the hypothesis that the quinoline group of the substrate is crucial to stabilize the acyl metal complex and prevent further decarbonylation. For [Pd]/BPh3-catalyzed alkoxycyanation, our findings clarify how the Lewis acid BPh3 cocatalyst accelerates the only slow step of the reaction, corresponding to the oxidative addition of the cyanate O-CN bond to the Pd center. © 2015 American Chemical Society.
    Citation
    Vummaleti SVC, Al-Ghamdi M, Poater A, Falivene L, Scaranto J, et al. (2015) Mechanism of Intramolecular Rhodium- and Palladium-Catalyzed Alkene Alkoxyfunctionalizations. Organometallics 34: 5549–5554. Available: http://dx.doi.org/10.1021/acs.organomet.5b00749.
    Sponsors
    European Commission[CIG09-GA-2011-293900]
    Ministerio de Economía y Competitividad[CTQ2014-59832-JIN]
    King Abdullah University of Science and Technology
    Publisher
    American Chemical Society (ACS)
    Journal
    Organometallics
    DOI
    10.1021/acs.organomet.5b00749
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/acs.organomet.5b00749
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.organomet.5b00749
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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