Citation: Liu Xuemin, Chen Wen, Ni Bangqing, Chen Xinzhi, Qian Chao, Ge Xin. Cu-Catalyzed Aqueous Phase Ullmann-Type C-N Coupling Reaction Promoted by Glycosyl Ligand[J]. Chinese Journal of Organic Chemistry, ;2018, 38(7): 1703-1711. doi: 10.6023/cjoc201801031 shu

Cu-Catalyzed Aqueous Phase Ullmann-Type C-N Coupling Reaction Promoted by Glycosyl Ligand

Liu Xuemin ^a ,
Chen Wen ^a ,
Ni Bangqing ^a ,
Chen Xinzhi ^b ,
Qian Chao ^b ,
Ge Xin ^a,,

a.
School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122
b.
Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, Zhejiang University, Hangzhou 310027

Corresponding author: Ge Xin, gexin@jiangnan.edu.cn
Received Date: 23 January 2018
Revised Date: 5 March 2018
Available Online: 4 July 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21476194, 21606104), the National Key Research and Development Program of China (No. 2016YFB0301800) and the Opening Foundation from Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology (No. ACEMT-17-03)the National Key Research and Development Program of China 2016YFB0301800the National Natural Science Foundation of China 21606104the Opening Foundation from Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology ACEMT-17-03the National Natural Science Foundation of China 21476194

Figures(2)

A green and efficient catalytic system has been developed for the Cu-catalyzed Ullmann-type C-N coupling reactions in water. With CuI as catalyst, N-(2-hydroxyethyl)-β-D-glucopyranosylamine as ligand, aryl iodides and aryl bromides bearing various electron-withdrawing and electron-donating groups could be coupled with N-nucleophiles in water with good yields (61%~96%). The catalytic system was expanded successfully to the reaction of indoles with 4-iodoanisole in water.
- copper,
- Ullmann reaction,
- glycosyl ligand,
- water
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