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    Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

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    Type
    Article
    Authors
    Nolan, Steven Patrick
    Izquierdo, Frederic
    Zinser, Caroline
    Minenkov, Yury cc
    Cordes, David B. cc
    Slawin, Alexandra
    Cavallo, Luigi cc
    Nahra, Fady cc
    Cazin, Catherine S. J. cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2017-12-19
    Online Publication Date
    2017-12-19
    Print Publication Date
    2018-02-07
    Permanent link to this record
    http://hdl.handle.net/10754/625458
    
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    Abstract
    The influence of C4,5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction have been investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands were synthesized. After determining electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr)(cin)Cl]. The three palladium complexes were studied using DFT calculations to delineate their behaviour in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.
    Citation
    Nolan SP, Izquierdo F, Zinser C, Minenkov Y, Cordes D, et al. (2017) Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction. ChemCatChem. Available: http://dx.doi.org/10.1002/cctc.201701279.
    Sponsors
    We gratefully acknowledge the European Commission (EC) for funding through the seventh framework program SYNFLOW, the European Research Council (ERC) (Advanced Investigator Award “FUNCAT” to S. P. N.), The Engineering and Physical Sciences Research Council (EPSRC) and AstraZeneca (Studentship to C. M. Z.). We thank the EPSRC National Mass Spectrometry Service Centre in Swansea for mass spectrometric analyses. We thank King Saud University and King Abdullah University of Science and Technology (Award No. OSR-2015-CCF-1974-03.)
    Publisher
    Wiley
    Journal
    ChemCatChem
    DOI
    10.1002/cctc.201701279
    Additional Links
    http://onlinelibrary.wiley.com/doi/10.1002/cctc.201701279/abstract
    Relations
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc1k03ym HANDLE: 10754/663818
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc1k0670 HANDLE: 10754/663819
    ae974a485f413a2113503eed53cd6c53
    10.1002/cctc.201701279
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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