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
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  • 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

  网络出版日期: 2013-07-10

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
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  • Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000

Received date: 2013-06-07

  Revised date: 2013-07-04

  Online 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).

摘要

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.

本文引用格式

韦珊红 , 王晨 , 王建伟 , 程凯 . 芳基氟硼酸盐同芳香胺“一锅法”Suzuki-Miyaura反应[J]. 有机化学, 2013 , 33(11) : 2402 -2406 . DOI: 10.6023/cjoc201306008

Abstract

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.

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