有机化学 ›› 2013, Vol. 33 ›› Issue (11): 2430-2434.DOI: 10.6023/cjoc201305052 上一篇    下一篇

研究简报

四丁基碘化铵催化的sp3-C—H键的磷酸酯化

王倩, 徐洲   

  1. 徐州医学院基础学院生化与化学综合实验室 徐州 221004
  • 收稿日期:2013-05-30 修回日期:2013-07-08 出版日期:2013-11-25 发布日期:2013-07-11
  • 通讯作者: 王倩 E-mail:qianwangchem@163.com
  • 基金资助:

    江苏省高校自然科学基金(No. 10KJB150018)资助项目.

Tetrabutylammonium Iodide-Catalyzed Phosphonation of sp3-C—H Bonds

Wang Qian, Xu Zhou   

  1. Experimental Center for Biochemistry and Chemistry Teaching, School of Basic Sciences, Xuzhou Medical College, Xuzhou 221004
  • Received:2013-05-30 Revised:2013-07-08 Online:2013-11-25 Published:2013-07-11
  • Supported by:

    Project supported by the Natural Science Foundation of Higher Education Institutions of Jiangsu Province (No. 10KJB150018).

以四丁基碘化铵(TBAI)为催化剂,过氧叔丁醇(TBHP)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-C—H键与亚磷酸酯的氧化偶联,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—P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α-氨基磷酸酯化合物.

关键词: sp3-C—H活化, 氧化偶联, 亚磷酸酯, 四丁基碘化铵

Activation of sp3-C—H bonds and oxidative phosphonation of sp3-C—H bonds adjacent to a nitrogen atom of tertiary amine were catalyzed by tetrabutylammonium iodide (TBAI) with t-butylhydroperoxide (TBHP) 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, oxidative coupling, phosphate, TBAI