有机化学 ›› 2016, Vol. 36 ›› Issue (6): 1341-1350.DOI: 10.6023/cjoc201601001 上一篇    下一篇

研究论文

无配体钯催化乙醇水溶液中芳基三氟硼酸钾的Suzuki反应

李新民, 刘春, 刘超, 金子林   

  1. 大连理工大学精细化工国家重点实验室大连 116012
  • 收稿日期:2016-01-02 修回日期:2016-01-20 出版日期:2016-06-25 发布日期:2016-02-24
  • 通讯作者: 刘春 E-mail:cliu@dlut.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21276043,21421005)及大连理工大学离退休科研基金(No.DUTTX2015102)资助项目.

Palladium-Catalyzed Ligand-Free Suzuki Reaction of Potassium Aryltrifluoroborates in Aqueous Ethanol

Li Xinmin, Liu Chun, Liu Chao, Jin Zilin   

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012
  • Received:2016-01-02 Revised:2016-01-20 Online:2016-06-25 Published:2016-02-24
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21276043, 21421005) and the Research Foundation of Dalian University of Technology for Retired Professors (No. DUTTX2015102).

发展了一个无配体钯催化芳基三氟硼酸钾的Suzuki反应体系. 该体系在空气条件下, 以醋酸钯为催化剂, 1 equiv.的无水碳酸钾为碱, 在乙醇水溶液中可高效催化卤代芳烃或杂环卤代芳烃与芳基三氟硼酸钾的Suzuki反应, 周转频率(TOF)值最高达4656 h-1, 且该体系还适用于三苯胺衍生物的合成. 透射电镜分析结果及汞中毒实验证明该体系的实际催化物质为原位生成的纳米钯粒子.

关键词: 钯, 无配体, Suzuki反应, 芳基三氟硼酸钾, 乙醇水溶液

A simple and ligand-free protocol has been developed for the Pd(OAc)2-catalyzed Suzuki reaction of potassium aryltrifluoroborates in aqueous ethanol under air. In the presence of Pd(OAc)2 and 1 equiv. of K2CO3, aryl or heteroaryl halides coupled with various potassium aryltrifluoroborates smoothly to afford the products in high yields with the highest turnover frequency (TOF) up to 4656 h-1, and a series of triphenylamine derivatives were prepared efficiently in this system. In addition, the active catalyst was proved to be the in situ-generated palladium nanoparticles according to TEM analysis and mercury-poisoning test.

Key words: palladium, ligand-free, Suzuki reaction, potassium aryltrifluoroborates, aqueous ethanol