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    An efficient protocol for the palladium-catalysed Suzuki-Miyaura cross-coupling

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    Type
    Article
    Authors
    Marziale, Alexander N.
    Jantke, Dominik
    Faul, Stefan Holger
    Reiner, Thomas cc
    Herdtweck, Eberhardt
    Eppinger, Jörg cc
    KAUST Department
    Biological & Organometallic Catalysis Laboratories
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2011
    Permanent link to this record
    http://hdl.handle.net/10754/561598
    
    Metadata
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    Abstract
    The palladacyclic catalyst precursor received by ortho-palladation of ([1,1′-biphenyl]-2-yloxy)diisopropyl-phosphine represents a highly active system for Suzuki-Miyaura cross-coupling reactions when used in neat water. An efficient, broadly applicable and sustainable aqueous protocol was developed using 2.5 eq. of Na2CO3 as base, allowing the reaction to be performed under air and at ambient temperature with Pd loadings of 0.04 mol%. Coupling products are obtained in high yields and excellent purity by simple filtration with no organic solvents needed throughout the whole reaction. A broad variety of functional groups are tolerated and a large number of substrates can be applied with this protocol. The crystal structure of the palladacyclic catalyst precursor is presented as well as investigations targeting the nature of catalyst activation and the active catalytic species. © 2011 The Royal Society of Chemistry.
    Citation
    Marziale, A. N., Jantke, D., Faul, S. H., Reiner, T., Herdtweck, E., & Eppinger, J. (2011). An efficient protocol for the palladium-catalysed Suzuki–Miyaura cross-coupling. Green Chem., 13(1), 169–177. doi:10.1039/c0gc00522c
    Sponsors
    We are grateful to the Elitenetzwerk Bayern (graduate fellowship for A.N.M.), KAUST (graduate fellowship for A.N.M. and D.J.) and the IDK NanoCat for funding of this project. Experimental support by Markus Scheibel is gratefully acknowledged. Finally we are particularly grateful to the Aramco PMT team, KAUST HSE and KAUST Procurement, who all worked very hard for more than a year to finishing our research laboratories.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Green Chem.
    DOI
    10.1039/c0gc00522c
    Relations
    Is Supplemented By:
    • [Dataset]
      Marziale, A. N., Jantke, D., Faul, S. H., Reiner, T., Herdtweck, E., & Eppinger, J. (2011). CCDC 788104: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvg2q2. DOI: 10.5517/ccvg2q2 HANDLE: 10754/624622
    • [Dataset]
      Marziale, A. N., Jantke, D., Faul, S. H., Reiner, T., Herdtweck, E., & Eppinger, J. (2011). CCDC 788105: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccvg2r3. DOI: 10.5517/ccvg2r3 HANDLE: 10754/624623
    ae974a485f413a2113503eed53cd6c53
    10.1039/c0gc00522c
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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