Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (5): 1213-1219.DOI: 10.6023/cjoc201612052 Previous Articles     Next Articles



李瑶, 马丽芳, 王晓姣, 雷搏文, 赵怡, 杨嘉宇, 李子元   

  1. 四川大学化学工程学院 制药与生物工程系 成都 610065
  • 收稿日期:2016-12-20 修回日期:2017-03-09 发布日期:2017-03-14
  • 通讯作者: 马丽芳,李子元;
  • 基金资助:


Palladium(II)-Catalyzed Homocoupling of Oxazole/Thiazole in Absence of Silver Oxidant

Li Yao, Ma Lifang, Wang Xiaojiao, Lei Bowen, Zhao Yi, Yang Jiayu, Li Ziyuan   

  1. Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065
  • Received:2016-12-20 Revised:2017-03-09 Published:2017-03-14
  • Contact: 10.6023/cjoc201612052;
  • Supported by:

    Project supported by the Fundamental Research Funds for the Central Universities (No. 2016SCU11020).

Homocoupling of oxazole/thiazole via palladium-catalyzed C-H bond activation using oxone as an oxidant has been achieved in moderate to excellent yields with good functional group tolerance. No other additive or ligand was employed in this efficient reaction. Comparing to our previously reported homocoupling of oxazole/thiazole, the absence of stoichiometric silver oxidant renders this reaction more environment-benign and cost-effective. A preliminary mechanism involving a Pd/Pd catalytic cycle is also proposed. Further exploration of this environmental-benign oxidant on other categories of coupling reactions, as well as applications of this revised homocoupling to structural modification of oxazole/thiazole-containing natural products, are undergoing in our lab.

Key words: thiazole, oxazole, homocoupling, C-H bond activation, oxone