Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones.

  • Yang F
  • Ji K
  • Ali S
 et al. 
  • 5

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Abstract

Highly substituted indole derivatives bearing alkyl and aryl moieties can be prepared by Sc(OTf)(3)-catalyzed Friedel-Crafts alkenylation of 5-(arylamino)pent-3-yn-2-ones. In addition, a method for regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones mediated by SnCl(4) in moderate to good yields (up to 84%) has been developed. The resulting exclusive Z-selectivity of the C-Cl bond can be further exploited using cross C-N coupling reactions.

Author-supplied keywords

  • Catalysis
  • Chemistry, Pharmaceutical
  • Chemistry, Pharmaceutical: methods
  • Halogenation
  • Indoles
  • Indoles: analysis
  • Indoles: chemical synthesis
  • Ketones
  • Ketones: chemistry
  • Magnetic Resonance Spectroscopy
  • Mesylates
  • Mesylates: chemistry
  • Molecular Structure
  • Scandium
  • Scandium: chemistry
  • Stereoisomerism
  • Tin Compounds
  • Tin Compounds: chemistry

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Authors

  • Fang Yang

  • Ke-Gong Ji

  • Shaukat Ali

  • Yong-Min Liang

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