有机化学 ›› 2015, Vol. 35 ›› Issue (3): 688-697.DOI: 10.6023/cjoc201412023 上一篇    下一篇

研究论文

铑(III)催化吲哚甲酰胺衍生物与末端炔烃的C—H活化/环化反应

王亮a,b, 瞿星a, 李站a, 彭望明a   

  1. a 江汉大学光电化学材料省部共建教育部重点实验室 武汉 430056;
    b 江汉大学化学与环境工程学院 武汉 430056
  • 收稿日期:2014-12-14 修回日期:2014-01-04 出版日期:2015-03-25 发布日期:2015-01-09
  • 通讯作者: 王亮, 彭望明 E-mail:wangliang@jhun.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21302064)资助项目.

Rhodium(III)-Catalyzed C—H Activation/Cylization of Indole-2-amides Derivatives and Terminal Alkynes

Wang Lianga,b, Qu Xinga, Li Zhana, Peng Wangminga   

  1. a Key Laboratory of Optoelectronic Chemical Materials and Devices of Ministry of Education, Jianghan University, Wuhan 430056;
    b School of Chemical and Enviromental Engineering, Jianghan University, Wuhan 430056
  • Received:2014-12-14 Revised:2014-01-04 Online:2015-03-25 Published:2015-01-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21302064)

报道了铑(III)催化的吲哚甲酰胺衍生物与末端的炔烃发生的C—H活化/环化反应, 能够高效地构建多环吲哚类化合物, 收率为85%~98%. 该反应操作简便、反应条件温和、催化剂用量低, 并使用具有氧化性的导向基团, 不需要添加额外氧化剂. 研究了该反应的分子间的竞争性试验, 推测了可能的反应机理. 所有化合物均采用NMR, IR, 高分辨质谱等多种谱学技术进行了结构表征.

关键词: 铑催化剂, 氧化性导向基团, C—H活化, 多环吲哚

A simple and efficient Rh-catalyzed the C—H activation/cyclization reaction of indole-2-amides and alkynes was developed. A series of novel pyrido[3,4-b]indol-1-ones can be efficiently obtained with high to excellent yields using the internal oxidant at room temperature. The transformations have a wide range of substrates with various functional groups. Intermolecular competition experiment was conducted, and a plausible mechanism was proposed. The structures of all conpound were confirmed by 1H NMR, 13C NMR and HRMS.

Key words: rhodium catalyst, oxidative directing group, C—H activation, polycyclic indoles