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    Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

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    Type
    Article
    Authors
    Xu, Jun
    Shen, Chao cc
    Zhu, Xiaolei
    Zhang, Pengfei
    Ajitha, Manjaly John
    Huang, Kuo-Wei cc
    An, Zhongfu
    Liu, Xiaogang cc
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-02-04
    Online Publication Date
    2016-02-04
    Print Publication Date
    2016-03-18
    Permanent link to this record
    http://hdl.handle.net/10754/621709
    
    Metadata
    Show full item record
    Abstract
    Achieving site selectivity in carbon-hydrogen (C-H) functionalization reactions is a formidable challenge in organic chemistry. Herein, we report a novel approach to activating remote C-H bonds at the C5 position of 8-aminoquinoline through copper-catalyzed sulfonylation under mild conditions. Our strategy shows high conversion efficiency, a broad substrate scope, and good toleration with different functional groups. Furthermore, our mechanistic investigations suggest that a single-electron-transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C-S cross-coupling. Importantly, our copper-catalyzed remote functionalization protocol can be expanded for the construction of a variety of chemical bonds, including C-O, C-Br, C-N, C-C, and C-I. These findings provide a fundamental insight into the activation of remote C-H bonds, while offering new possibilities for rational design of drug molecules and optoelectronic materials requiring specific modification of functional groups. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Xu J, Shen C, Zhu X, Zhang P, Ajitha MJ, et al. (2016) Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling. Chemistry - An Asian Journal 11: 882–892. Available: http://dx.doi.org/10.1002/asia.201501407.
    Sponsors
    We thank the funding support from the National Natural Science Foundation of China (No. 21376058, 21302171), Zhejiang Provincial Natural Science Foundation of China (No. LZ13B 020001) and the Key-Sci-Tech Innovation Team of Zhejiang Province (No. 2010R50017).
    Publisher
    Wiley
    Journal
    Chemistry - An Asian Journal
    DOI
    10.1002/asia.201501407
    10.1002/asia.201600224
    PubMed ID
    26756288
    Additional Links
    http://onlinelibrary.wiley.com/doi/10.1002/asia.201501407/full
    Relations
    Is Supplemented By:
    • [Dataset]
      Xu, J., Shen, C., Zhu, X., Zhang, P., Ajitha, M. J., Huang, K.-W., … Liu, X. (2016). CCDC 1041995: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc13z8r3. DOI: 10.5517/ccdc.csd.cc13z8r3 HANDLE: 10754/624496
    • [Dataset]
      Xu, J., Shen, C., Zhu, X., Zhang, P., Ajitha, M. J., Huang, K.-W., … Liu, X. (2016). CCDC 1429311: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1jz9tm. DOI: 10.5517/ccdc.csd.cc1jz9tm HANDLE: 10754/624525
    ae974a485f413a2113503eed53cd6c53
    10.1002/asia.201501407
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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