Citation: Li Yao, Ma Lifang, Wang Xiaojiao, Lei Bowen, Zhao Yi, Yang Jiayu, Li Ziyuan. Palladium(Ⅱ)-Catalyzed Homocoupling of Oxazole/Thiazole in Absence of Silver Oxidant[J]. Chinese Journal of Organic Chemistry, ;2017, 37(5): 1213-1219. doi: 10.6023/cjoc201612052 shu

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

Department of Pharmaceutical and Biological Engineering, School of Chemical Engineering, Sichuan University, Chengdu 610065

Corresponding author: Ma Lifang, mlfang11@scu.edu.cn Li Ziyuan, liziyuan@scu.edu.cn
Received Date: 20 December 2016
Revised Date: 9 March 2017

Fund Project: by the Fundamental Research Funds for the Central Universities 2016SCU11020

Figures(3)

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^Ⅱ/Pd^Ⅳ 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.
- thiazole,
- oxazole,
- homocoupling,
- C-H bond activation,
- oxone
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