有机化学 ›› 2019, Vol. 39 ›› Issue (11): 3244-3249.DOI: 10.6023/cjoc201903024 上一篇    下一篇

研究论文

铜催化的有氧氧化合成靛红类衍生物的方法

AhmadMuhammad Siddique, 主亚敏, 郭云龙, 张赛赛, 沈增明*()   

  1. 上海交通大学化学化工学院 上海 200240
  • 收稿日期:2019-03-14 出版日期:2019-11-25 发布日期:2019-06-12
  • 通讯作者: 沈增明 E-mail:shenzengming@sjtu.edu.cn
  • 基金资助:
    国家自然科学基金(21672144)

Copper-Catalyzed Aerobic Oxidation Strategy: A Concise Route to Isatin

Ahmad Muhammad Siddique, Zhu Yamin, Guo Yunlong, Zhang Saisai, Shen Zengming*()   

  1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
  • Received:2019-03-14 Online:2019-11-25 Published:2019-06-12
  • Contact: Shen Zengming E-mail:shenzengming@sjtu.edu.cn
  • Supported by:
    the National Natural Sciences Foundation of China(21672144)

研究了铜催化的脱羰环化生成靛红的方法,使用氧气作为最终的氧化剂.这个互补的C(sp3)—H官能团化方法为合成靛红提供了一种新方案.Cu/O2/Co体系显示出良好的反应性和兼容性,富电子和缺电子的官能团都可以很好地兼容.并基于机理研究和以前的文献报道,提出了一个可能的假设机理.

关键词: 铜催化, 碳氢键活化, 靛红, 脱羰, 氧气

A copper-catalyzed decarbonylation cyclization to form isatins using oxygen as terminal oxidant is developed. This complementary way offers a new protocol for the synthesis of isatins through C(sp3)—H bond functionalization in Cu/O2/Co system. This system shows good reactivity and compatibility. Both electron-rich and electron-deficient functional groups can be tolerated. A postulated mechanism is proposed based on mechanistic studies and previous reports.

Key words: Cu catalyst, C—H bond activation, isatin, decarbonylation, oxygen