title: Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones.
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.
authors: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Chinese Academy of Science, Lanzhou 730000, People's Republic of China.
authors: Fang
authors: F
authors: Yang
authors: Ke-Gong
authors: KG
authors: Ji
authors: Shaukat
authors: S
authors: Ali
authors: Yong-Min
authors: YM
authors: Liang
mesh_terms: D002384:Catalysis; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D054879:Halogenation; D007211:Indoles / Q000032:analysis / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012538:Scandium / Q000737:chemistry*; D013237:Stereoisomerism; D017971:Tin Compounds / Q000737:chemistry*
chemical_list: D007211:Indoles; D007659:Ketones; D008698:Mesylates; D017971:Tin Compounds; C436603:scandium triflate; C041694:stannic chloride; D012538:Scandium