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

doi:10.6023/cjoc201801031

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1703-1711.DOI: 10.6023/cjoc201801031 Previous Articles Next Articles

Articles

糖基配体促进的铜催化水相Ullmann型C-N偶联反应

刘学民^a, 陈雯^a, 倪邦庆^a, 陈新志^b, 钱超^b, 葛新^a

a 江南大学化学与材料工程学院无锡 214122;
b 浙江大学浙江省化工高效制造技术重点实验室杭州 310027

收稿日期:2018-01-23 修回日期:2018-03-05 发布日期:2018-04-04
通讯作者: 葛新 E-mail:gexin@jiangnan.edu.cn
基金资助:
国家自然科学基金（Nos.21476194，21606104），国家重点研发计划（No.2016YFB0301800）和浙江省化工高效制造技术重点实验室开放课题（No.ACEMT-17-03）资助项目.

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

Received:2018-01-23 Revised:2018-03-05 Published:2018-04-04
Contact: 10.6023/cjoc201801031 E-mail:gexin@jiangnan.edu.cn
Supported by:
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).

1. Cu-Catalyzed Aqueous Phase Ullmann-Type C-N Coupling Reaction Promoted by Glycosyl Ligand.PDF(1832KB)

Abstract

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.

Key words: copper, Ullmann reaction, glycosyl ligand, water

Cite this article

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]. Chin. J. Org. Chem., 2018, 38(7): 1703-1711.

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糖基配体促进的铜催化水相Ullmann型C-N偶联反应

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

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