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RuII-Catalyzed/NH2-Assisted Selective Alkenyl C–H [5 + 1] Annulation of Alkenylanilines with Sulfoxonium Ylides to Quinolines

  • Pu Chen
    Pu Chen
    Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    More by Pu Chen
  • , 
  • Jiang Nan*
    Jiang Nan
    Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    *E-mail: [email protected]
    More by Jiang Nan
    Orcidhttp://orcid.org/0000-0001-5570-6834
  • , 
  • Yan Hu
    Yan Hu
    Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    More by Yan Hu
  • , 
  • Qiong Ma
    Qiong Ma
    Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    More by Qiong Ma
  • , and 
  • Yangmin Ma*
    Yangmin Ma
    Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an 710021, China
    *E-mail: [email protected]
    More by Yangmin Ma
Cite this: Org. Lett. 2019, 21, 12, 4812–4815
Publication Date (Web):June 13, 2019
https://doi.org/10.1021/acs.orglett.9b01702
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    Abstract

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    A novel ruthenium-catalyzed [5 + 1] annulation of 2-alkenylanilines with sulfoxonium ylides was developed for the rapid assembly of highly functionalized quinolines. This new catalytic process employs challenging but synthetically ideal free amino functionality to achieve alkenyl C–H activation with sulfoxonium ylides as one-carbon coupling partners. Various 2-acylquinolines could be obtained with good yields and excellent functional group tolerance. Moreover, the potential synthetic application of this methodology was exemplified by several chemical transformations.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.9b01702.

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    CCDC 1914297 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336033.

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