铑(III)催化吲哚甲酰胺衍生物与末端炔烃的C—H活化环化反应有机化学.pdfVIP

DOI: 10.6023/cjoc201412023 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 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 (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) 摘要 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 Rhodium(III)-Catalyzed C—H Activation/Cylization of Indole-2-amides Derivatives and Terminal Alkynes Wang, Liang*,a,b Qu, Xinga Li, Zhana Peng, Wangming*,a 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) Abstract 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 in- ternal oxidant at room temperature. The transformations have a wide range of substrates with various functional groups. Inter- molecular competition experiment was conducted, and a plausible mechanism was proposed. The structures of all conpound were confirmed by 1H NM