有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1551-1562.DOI: 10.6023/cjoc202010027 上一篇    下一篇

研究论文

镍催化的卤代糖苷和卤代芳烃通过还原偶联制备芳香碳糖苷类化合物的简易方法

孙雨人a, 刘建东a, 林泉a, 姚建a, 童玮琦b, 钱群b,*()   

  1. a 上海大学材料科学与工程学院 上海大学超分子化学与催化研究中心 上海 200444
    b 上海大学理学院 上海 200444
  • 收稿日期:2020-10-20 修回日期:2020-11-12 发布日期:2020-12-05
  • 通讯作者: 钱群
  • 基金资助:
    国家自然科学基金(21871173)

Facile Preparation of Aryl C-Glycosides by Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Aryl Halides

Yuren Suna, Jiandong Liua, Quan Lina, Ken Yaoa, Weiqi Tongb, Qun Qianb,*()   

  1. a School of Materials Science and Engineering, Center for Supramolecular Chemistry and Catalysis, Shanghai 200444
    b College of Sciences, Shanghai University, Shanghai 200444
  • Received:2020-10-20 Revised:2020-11-12 Published:2020-12-05
  • Contact: Qun Qian
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(21871173)

报道了在温和条件下通过镍和联吡啶催化的还原偶联反应, 由C(1)-卤代糖苷和缺电子的芳基溴化物制备芳香糖苷类化合物的方法. 运用该种方法可以由中等或高的α-选择性得到芳香碳糖苷类产物. 包括富电子的芳香碘化物在内的多种卤代芳烃底物适用于该反应, 产率在40%~95%之间. 该方法可以放大到克级规模, 并在此条件下将镍催化剂的用量减少到2 mol%.

关键词: 镍催化, 还原偶联, α-选择性制备, 芳香碳糖苷, 克级反应

The preparation of C-aryl glycosides via mild Ni/bipyridine-catalyzed reductive arylation of C(1)-glycosyl halides with electron-deficient aryl bromides was developed. Moderate to high α-selectivities were achieved for C-glycosides. A broad range of aryl halides including electron-rich aryl iodides were employed to yield C-aryl glycosides in 40%~5% yields. This method can be scaled up on a gram scale by lowering the loading of nickel catalyst to 2 mol%.

Key words: nickel-catalysis, reductive coupling, α-selective preparation, C-aryl glycoside, gram scale