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    Cyclopentadienyl molybdenum(II/VI) N-heterocyclic carbene complexes: Synthesis, structure, and reactivity under oxidative conditions

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    Type
    Article
    Authors
    Li, Shenyu
    Kee, Choonwee
    Huang, Kuo-Wei cc
    Hor, Andy Sum Andy
    Zhao, Jin
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2010-04-26
    Permanent link to this record
    http://hdl.handle.net/10754/561467
    
    Metadata
    Show full item record
    Abstract
    A series of N-heterocyclic carbene (NHC) complexes CpMo(CO) 2(NHC)X (NHC = IMe = 1,3-dimethylimidazol-2-ylidene, X = Br, 1; NHC = 1,3-dipropylimidazol-2-ylidene, X = Br, 2; NHC = IMes = 1,3-bis(2,4,6- trimethylphenyl)imidazol-2-ylidene, X = Br, 3; NHC = IBz = 1,3-dibenzylimidazol- 2-ylidene, X = Br, 4a, and X = Cl, 4b; NHC = 1-methyl-3-propylimidazol-2- ylidene, X = Br, 5) and [CpMo(CO)2(IMes)(CH3CN)][BF 4] (6) have been synthesized and fully characterized. The stability of metal-NHC ligand bonds in these compounds under oxidative conditions has been investigated. The thermally stable Mo(VI) dioxo NHC complex [CpMoO 2(IMes)][BF4] (9) has been isolated by the oxidation of the ionic complex 6 by TBHP (tert-butyl hydrogen peroxide). Complex 6 can be applied as a very active (TOFs up to 3400 h-1) and selective olefin epoxidation catalyst. While under oxidative conditions (in the presence of TBHP), compounds 1-5 decompose into imidazolium bromide and imidazolium polyoxomolybdate. The formation of polyoxomolybdate as oxidation products had not been observed in a similar epoxidation catalyzed by Mo(II) and Mo(VI) complexes. DFT studies suggest that the presence of Br- destabilizes the CpMo(VI) oxo NHC carbene species, consistent with the experimental observations. © 2010 American Chemical Society.
    Citation
    Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2010). Cyclopentadienyl Molybdenum(II/VI) N-Heterocyclic Carbene Complexes: Synthesis, Structure, and Reactivity under Oxidative Conditions. Organometallics, 29(8), 1924–1933. doi:10.1021/om900980a
    Sponsors
    We are grateful to the Ministry of Education (MOE) of Singapore Academic Research Fund (AcRF) Tier 1 Grant (WBS No. R-143-000-373-112). S.Y. L. also thanks National University of Singapore for the scholarship. K.W.H. acknowledges the support from KAUST baseline funding. We thank Ms. Geok Kheng Tan and Dr. Lip Lin Koh for determining the X-ray crystal structures.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organometallics
    DOI
    10.1021/om900980a
    Relations
    Is Supplemented By:
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 748781: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cct457b. DOI: 10.5517/cct457b HANDLE: 10754/624609
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 748782: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cct458c. DOI: 10.5517/cct458c HANDLE: 10754/624610
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 748783: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cct459d. DOI: 10.5517/cct459d HANDLE: 10754/624611
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 748784: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cct45bf. DOI: 10.5517/cct45bf HANDLE: 10754/624612
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 748785: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cct45cg. DOI: 10.5517/cct45cg HANDLE: 10754/624613
    • [Dataset]
      Li, S., Kee, C. W., Huang, K.-W., Hor, T. S. A., & Zhao, J. (2011). CCDC 810641: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw6jq9. DOI: 10.5517/ccw6jq9 HANDLE: 10754/624632
    ae974a485f413a2113503eed53cd6c53
    10.1021/om900980a
    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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