有机化学 ›› 2020, Vol. 40 ›› Issue (7): 2008-2017.DOI: 10.6023/cjoc202001030 上一篇    下一篇

研究论文

壳聚糖@铜催化吲哚与硫粉和芳基碘化物的C3-硫醚化反应

成琳a, 葛新a, 刘学民a, 冯云辉b   

  1. a 江南大学化学与材料工程学院 江苏无锡 214122;
    b 广州大学体育教育系 广州 510006
  • 收稿日期:2020-01-23 修回日期:2020-04-29 发布日期:2020-05-08
  • 通讯作者: 刘学民, 冯云辉 E-mail:lxm@jiangnan.edu.cn;13795553266@163.com
  • 基金资助:
    国家自然科学基金(No.21606104)资助项目.

Chitosan@Cu-Catalyzed C3-Sulfenylation of Indoles with Sulfur Powder and Aryl Iodides

Cheng Lina, Ge Xina, Liu Xuemina, Feng Yunhuib   

  1. a School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122;
    b Department of Physical Education, Guangzhou University, Guangzhou 510006
  • Received:2020-01-23 Revised:2020-04-29 Published:2020-05-08
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21606104).

针对以硫单质为硫源的吲哚环中C—S键构筑中催化剂无法回收的问题,制备了2-吡啶甲酸改性壳聚糖(PACS)负载不同类型铜的催化剂,用于催化吲哚、硫粉和碘苯三组分反应一锅法制备C-3位硫醚基吲哚,反应收率高达92%,底物适用性良好.对催化效果最佳的催化剂(PACS@Cu(OAc)2)进行了热重分析(TGA)、扫描电子显微镜(SEM)、X射线光电子能谱(XPS)等表征与分析,结果表明该催化剂具有不需额外添加配体、易于分离回收及可重复使用的优点.

关键词: 壳聚糖, 吲哚, 硫粉, 催化, 非均相

Aiming at the problem that the catalyst can not be recovered during the construction of the C-S bond in the indole ring with sulfur powder as the sulfur source, 2-pyridinecarboxylic acid modified chitosan (PACS) catalyst with different type of copper was prepared, which was used to catalyze the three-component reaction of indole, sulfur powder and iodobenzene to prepare C-3 thioether-based indole in a one-pot method. The reaction yield is as high as 92%, and the substrate has good applicability. The most suitable catalyst[PACS@Cu(OAc)2] was characterized and analyzed by thermogravimetric analysis (TGA), scanning electron microscope(SEM), X-ray photoelectron spectroscopy(XPS), etc. It shows that the catalyst has the advantages of no additional ligand, easy separation and reusable.

Key words: chitosan, indole, sulfur powder, catalyze, heterogeneous