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    Efficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexes

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    Type
    Article
    Authors
    Liu, Yanpin
    Chen, Chaohuang
    Li, Huaifeng cc
    Huang, Kuo-Wei cc
    Tan, Jianwei
    Weng, Zhiqiang
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2013-10-18
    Online Publication Date
    2013-10-18
    Print Publication Date
    2013-11-11
    Permanent link to this record
    http://hdl.handle.net/10754/563082
    
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    Abstract
    Copper(I) fluoride complexes ligated by phenanthroline derivatives have been synthesized and structurally characterized by X-ray crystallography. These complexes adopt as either ionic or neutral forms in the solid state, depending on the steric bulkiness of the substituent groups on the phenanthroline ligands. These complexes react with primary and secondary alkyl bromides to produce the corresponding alkyl fluorides in modest to good yields. This new method is compatible with a variety of important functional groups such as ether, thioether, amide, nitrile, methoxyl, hydroxyl, ketone, ester, and heterocycle moieties. © 2013 American Chemical Society.
    Sponsors
    We acknowledge the financial support from National Natural Science Foundation of China (21072030), Research Fund for the Doctoral Program of Higher Education of China (No. 20123514110003), SRF for ROCS, SEM (J20121707), the Science Foundation of the Fujian Province, China (2013J01040), and Fuzhou University (022318, 022494) to Z.W. and King Abdullah University of Science and Technology to K.-W.H.
    Publisher
    American Chemical Society (ACS)
    Journal
    Organometallics
    DOI
    10.1021/om4008967
    Relations
    Is Supplemented By:
    • [Dataset]
      Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949811: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc2b. DOI: 10.5517/cc10wc2b HANDLE: 10754/624240
    • [Dataset]
      Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949812: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc3c. DOI: 10.5517/cc10wc3c HANDLE: 10754/624241
    • [Dataset]
      Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949813: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc4d. DOI: 10.5517/cc10wc4d HANDLE: 10754/624242
    ae974a485f413a2113503eed53cd6c53
    10.1021/om4008967
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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