Chinese Journal of Organic Chemistry >
Cu-Catalyzed Aqueous Phase Ullmann-Type C-N Coupling Reaction Promoted by Glycosyl Ligand
Received date: 2018-01-23
Revised date: 2018-03-05
Online published: 2018-04-04
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).
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
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
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