Sc(OTf)3 催化吲哚合成和 SnCl4 介导的 5-(芳基氨基)戊-3-炔-2-酮区域选择性氯化反应。
Sc(OTf)3-catalyzed synthesis of indoles and SnCl4-mediated regioselective hydrochlorination of 5-(arylamino)pent-3-yn-2-ones.
机构信息
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Chinese Academy of Science, Lanzhou 730000, People's Republic of China.
出版信息
J Org Chem. 2011 Oct 21;76(20):8329-35. doi: 10.1021/jo201514q. Epub 2011 Sep 16.
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.
通过 Sc(OTf)(3)催化的 5-(芳氨基)戊-3-炔-2-酮的 Friedel-Crafts 烯丙基化反应，可以制备带有烷基和芳基部分的高取代吲哚衍生物。此外，还开发了一种在 SnCl(4)存在下对 5-(芳氨基)戊-3-炔-2-酮进行区域选择性氯化的方法，中等至良好的收率（高达 84%）。通过交叉 C-N 偶联反应，可以进一步利用 C-Cl 键的这种独特的 Z 选择性。
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