Synthesis of a Novel Diol-Functionalized Poly(ethylene glycol)-Bridged Dicationic Ionic Liquid and its Application in Copper-Catalyzed Amination of Aryl Halides
Yinglei Wang A , Jun Luo A B , Tianjiao Hou A and Zuliang Liu A
+ Author Affiliations
- Author Affiliations
A School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China.
B Corresponding author. Email: luojun@njust.edu.cn
Australian Journal of Chemistry 66(5) 586-593 https://doi.org/10.1071/CH12487
Submitted: 29 October 2012 Accepted: 25 January 2013 Published: 27 March 2013
Abstract
A novel diol-functionalized poly(ethylene glycol)-bridged dicationic ionic liquid ([diol-PEG1000-DIL][PF6]) is prepared and used as an efficient and reusable ligand for copper-catalyzed amination. A variety of aryl iodides and aryl bromides reacted smoothly with aqueous ammonia to afford the corresponding aromatic primary amines in good to excellent yields. It is remarkable that aryl chlorides with a strong electron-withdrawing group exhibited a dramatically elevated activity in the presence of tetrabutylammonium bromide. Furthermore, the catalyst could be easily recovered and reused without obvious loss of catalytic activity after five recycling runs.
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