有机化学 ›› 2012, Vol. 32 ›› Issue (11): 2090-2094.DOI: 10.6023/cjoc201210029 上一篇    下一篇

研究论文

Bu4NAuCl4催化的H2O2氧化的sp3-C—H键与sp3-C—H键的交叉偶联反应

张艳a,b, 朱成建b   

  1. a 江南大学医药学院 无锡 214122;
    b 南京大学化学化工学院 南京 210093
  • 收稿日期:2012-10-17 修回日期:2012-10-29 发布日期:2012-10-31
  • 通讯作者: 张艳 E-mail:zhangyanchem@163.com
  • 基金资助:

    国家自然科学基金(No. 21074054)和2012江苏省大学生创新训练资助项目.

Oxidative Cross Coupling of sp3-C—H Bonds Catalyzed by Bu4NAuCl4 with H2O2 as Oxidant

Zhang Yana,b, Zhu Chengjianb   

  1. a School of Medicine and Pharmaceutics, Jiangnan University, Wuxi 214122;
    b State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093
  • Received:2012-10-17 Revised:2012-10-29 Published:2012-10-31
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21074054) and the Innovation Experiment Program for University Students of Jiangsu Province.

以Bu4NAuCl4为催化剂, H2O2作为氧化剂, 在温和的反应条件下实现了叔胺氮的邻位碳原子上sp3-CH与硝基烷烃的氧化偶联. 反应条件温和, 室温、空气下即可进行, 适用范围广泛, 产率高, 后处理方便. 为新的C—C键的形成提供了一条简洁高效的反应路径, 并且合成了一系列可能具有重要药理和生物活性的β-硝基氨化合物.

关键词: sp3-C—H活化, 交叉脱氢偶联, 氧化烷基化, 金催化剂

Activation of two sp3-C—H bonds and oxidative alkylation of sp3-C—H bond adjacent to a nitrogen atom of tertiary amine were catalyzed by Bu4NAuCl4 with H2O2 as oxidant under mild reaction conditions. The safe, convenient, and environmentally benign process, as well as the broad substrate scope, low catalyst loading, high selectivity, short reaction time, and good yields make the protocol very practical.

Key words: sp3-C—H activation, cross-dehydrogenative coupling, oxidative alkylation, gold catalyst