有机化学 ›› 2013, Vol. 33 ›› Issue (11): 2402-2406.DOI: 10.6023/cjoc201306008 上一篇    下一篇

研究论文

芳基氟硼酸盐同芳香胺“一锅法”Suzuki-Miyaura反应

韦珊红, 王晨, 王建伟, 程凯   

  1. 绍兴文理学院 浙江省精细化学品传统工艺替代技术研究重点实验室 绍兴 312000
  • 收稿日期:2013-06-07 修回日期:2013-07-04 发布日期:2013-07-10
  • 通讯作者: 程凯 E-mail:chengkai@usx.edu.cn
  • 基金资助:

    国家自然科学基金(No. 21202102)、浙江省科技厅(No. 2012R10014-15)和绍兴市科技计划(No. 2013014017)资助项目.

“One-Pot” Suzuki-Miyaura Reaction with Aryltrifluoroborate Salts from Aromatic Amines

Wei Shanhong, Wang Chen, Wang Jianwei, Cheng Kai   

  1. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000
  • Received:2013-06-07 Revised:2013-07-04 Published:2013-07-10
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21202102), the Science Technology Department of Zhejiang Province (No. 2012R10014-15) and the Scienece Technology Project of Shaoxing City (No. 2013014017).

研究了一种钯催化的芳香胺通过“一锅法”的Suzuki-Miyaura反应制备联苯类化合物. 该反应以水作为溶剂,无需分离重氮盐中间体,直接加入芳基氟硼酸钾、碱和催化剂,即可较高产率地得到偶联产物. 反应无需加热和惰性气体保护,具有良好的官能团耐受性,是一种绿色高效的偶联方法. 我们通过热力学计算推测了碱的加入对于反应的促进作用.

关键词: 交叉偶联, 绿色化学, 重氮化合物

Palladium-catalyzed "one-pot" Suzuki-Miyaura reactions of various aromatic amines with aryltrifluoroborate salts have been achieved in good yields under simple aerobic conditions in water without heating. The reported cross-coupling reac-tions are tolerant to the common functional groups regardless of electron-withdrawing or electron donating, making these transformations as attractive alternatives to the traditional cross-coupling approaches. Theoretical calculation shows that the coordination of tert-butoxide can lower the transition state energy by 50 kJ/mol for the transmetalation step.

Key words: cross-coupling, green chemistry, diazo compounds