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    Stability and Reactivity of Cyclometallated Naphthylamine Complexes in Pd-C Bond Insertion Reactions with Coordinated Alkynylphosphanes

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    Type
    Article
    Authors
    Chen, Shuli
    Chiew, Jun Xuan
    Pullarkat, Sumod A.
    Li, Yongxin
    Leung, Pak Hing
    KAUST Department
    KAUST Catalysis Center (KCC)
    Date
    2013-09-17
    Online Publication Date
    2013-09-17
    Print Publication Date
    2013-11-04
    Permanent link to this record
    http://hdl.handle.net/10754/594189
    
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    Abstract
    Phenylbis(phenylethynyl)phosphane PhP(C≡CPh)2 coordinates regiospecifically to the α-methyl-chiral ortho-platinated and -palladated naphthylamine units at the positions trans to the nitrogen donors. The P→Pt coordination bond is kinetically inert, whereas the P→Pd bond is labile. Upon heating of these phosphane complexes at 70 °C, one of the C≡C bonds in the coordinated PhP(C≡CPh)2 was activated towards an intermolecular Pd-C bond insertion reaction with an external ortho-palladated naphthylamine ring. No intramolecular insertion reaction occurred. In contrast to its palladium analogue, the ortho-platinated ring is not reactive towards coordinated PhP(C≡CPh)2, although it can promote the Pd-C bond insertion reaction. However, despite the high kinetic stability of the P→Pt coordination, the organoplatinum unit is a noticeably weaker activator than its organopalladium counterpart. The chirality of the reacting ortho-metallated naphthylamine ligand exhibited high stereochemical influence on the formation of the new stereogenic phosphorus center during the course of these C-C bond-formation reactions. The coordination chemistry and the absolute stereochemistry of the dimetallic products were determined by single-crystal X-ray crystallographic analysis. The asymmetric monoinsertion of PhP(C≡CPh)2 coordinated to a cyclometallated N,N-dimethyl naphthyl/benzylamine template into the Pd-C bonds of N,N-dimethylnaphthylamine palladacycles has been demonstrated for the synthesis of a variety of new P-stereogenic homo- or heterodimetallic complexes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Chen S, Chiew JX, Pullarkat SA, Li Y, Leung P-H (2013) Stability and Reactivity of Cyclometallated Naphthylamine Complexes in Pd-C Bond Insertion Reactions with Coordinated Alkynylphosphanes. European Journal of Inorganic Chemistry 2013: 5487–5494. Available: http://dx.doi.org/10.1002/ejic.201300834.
    Publisher
    Wiley
    Journal
    European Journal of Inorganic Chemistry
    DOI
    10.1002/ejic.201300834
    Relations
    Is Supplemented By:
    • [Dataset]
      Chen, S., Chiew, J. X., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2013). CCDC 940295: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10kg34. DOI: 10.5517/cc10kg34 HANDLE: 10754/624225
    • [Dataset]
      Chen, S., Chiew, J. X., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2013). CCDC 940296: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10kg45. DOI: 10.5517/cc10kg45 HANDLE: 10754/624226
    • [Dataset]
      Chen, S., Chiew, J. X., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2013). CCDC 940297: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10kg56. DOI: 10.5517/cc10kg56 HANDLE: 10754/624227
    • [Dataset]
      Chen, S., Chiew, J. X., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2013). CCDC 940298: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10kg67. DOI: 10.5517/cc10kg67 HANDLE: 10754/624228
    • [Dataset]
      Chen, S., Chiew, J. X., Pullarkat, S. A., Li, Y., & Leung, P.-H. (2013). CCDC 940299: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10kg78. DOI: 10.5517/cc10kg78 HANDLE: 10754/624229
    ae974a485f413a2113503eed53cd6c53
    10.1002/ejic.201300834
    Scopus Count
    Collections
    Articles; KAUST Catalysis Center (KCC)

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