有机化学 ›› 2017, Vol. 37 ›› Issue (5): 1213-1219.DOI: 10.6023/cjoc201612052 上一篇    下一篇

所属专题: 热点论文合辑

研究论文

不使用银氧化剂的噻唑/噁唑钯催化二聚反应(英文)

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 E-mail:mlfang11@scu.edu.cn;liziyuan@scu.edu.cn
  • 基金资助:

    中央高校基本科研业务费(No.2016SCU11020)资助项目.

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 E-mail:mlfang11@scu.edu.cn;liziyuan@scu.edu.cn
  • Supported by:

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

以Oxone作为氧化剂,实现了基于钯催化C-H键活化的噻唑/噁唑二聚反应,具有中等至优异的收率和理想的官能团耐受性,且无需添加其它添加剂或配体.与本作者过去报道的二聚反应相比,本反应避免使用化学当量的银盐作为氧化剂,使得本反应更具经济性和环境友好性.此外,初步提出了一条涉及二价钯/四价钯催化循环的反应机理.进一步将该环境友好的氧化剂应用于其他类型的偶联反应,以及将其应用于含有噻唑/噁唑结构的天然产物结构修饰上,尚在进行中.

关键词: 噻唑, 噁唑, 二聚反应, C-H键活化, Oxone

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