Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1258-1265.DOI: 10.6023/cjoc201610039 Previous Articles     Next Articles



白亚丽a, 李晓维b, 肖雪冬a, 刘佳琦a, 杨俊娟a, 王君文a   

  1. a 山西师范大学化学与材料科学学院 临汾 041000;
    b 内蒙古大唐国际再生资源开发有限公司 呼和浩特 010000
  • 收稿日期:2016-10-22 修回日期:2016-12-06 发布日期:2017-02-08
  • 通讯作者: 王君文
  • 基金资助:


Synthesis of Imidazolium Precursors for the Hydroxyl-Group-Modified N-Heterocyclic Carbenes and Applications of the in situ Generated Carbene Ligands in Suzuki-Miyaura and Sonogashira Coupling Reactions

Bai Yalia, Li Xiaoweib, Xiao Xuedonga, Liu Jiaqia, Yang Junjuana, Wang Junwena   

  1. a Department of Chemistry, Shanxi Normal University, Linfen 041000;
    b Inner Mongolia Datang International Renewable Resources Development Co. Ltd., Hohhot 010000
  • Received:2016-10-22 Revised:2016-12-06 Published:2017-02-08
  • Contact: 10.6023/cjoc201610039
  • Supported by:

    Project supported by the Basic Research Project of Shanxi Province of China (No. 2015011029), the Undergraduate Innovative Experiment Program of Shanxi Normal University (No. SD2014CXXM-36) and the Shanxi Province Education Innovation Project for Postgraduate (No. 2015BY38).

Four imidazolium precursors for the N-heterocyclic carbenes (NHCs) with a hydroxyl functionalized four-mem-bered heterocyclic side arm were synthesized and characterized by IR, XRD and NMR spectroscopies. The corresponding NHC ligands thus generated in situ from these imidazolium precursors in the presence of base such as KOH, together with PdCl2(CH3CN)2, exhibited excellent catalytic activity in Suzuki-Miyaura cross-coupling reactions for the synthesis of a range of biaryl compounds. The reactions could be conducted in the mixed solvent of tert-butyl alcohol/water (V:V=1:1) at room temperature with the advantages of mild conditions, high efficiency as well as environmental friendliness. In addition, although in minor amount, the mixed catalyst system containing imidazolium salts, PdCl2(CH3CN)2 (0.1%) and CuI (1%) exhibited excellent catalytic activity in Sonogashira coupling reaction. In particular, the combination system of PdCl2/imidazolium salt 3b has been shown to be higher catalytically active for both coupling reactions.

Key words: hydroxyl group, N-heterocyclic carbene, palladium, Suzuki-Miyaura cross-coupling, Sonogashira cross-coupling