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2018 , Vol. 38 >Issue 7: 1703 - 1711

DOI: https://doi.org/10.6023/cjoc201801031

研究论文

糖基配体促进的铜催化水相Ullmann型C-N偶联反应

  • 刘学民 ,
  • 陈雯 ,
  • 倪邦庆 ,
  • 陈新志 ,
  • 钱超 ,
  • 葛新
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  • 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

  网络出版日期: 2018-04-04

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.

收起

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

  • Liu Xuemin ,
  • Chen Wen ,
  • Ni Bangqing ,
  • Chen Xinzhi ,
  • Qian Chao ,
  • Ge Xin
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  • 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 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).

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摘要

开发了一种用于实现水相中的铜催化Ullmann型C-N偶联反应的绿色且高效的催化体系.以CuI为催化剂、N-（2-羟乙基）-β-D-吡喃葡萄糖胺为配体，芳基碘化物、芳基溴化物与N-亲核试剂都能在水中实现偶联反应，芳基碘化物的吸电子取代和供电子取代效应影响较小.偶联产物的收率良好（61%～96%）.该催化体系也成功扩展到各种吲哚与4-碘苯甲醚的水相偶联反应中.绿色且可降解的配体、温和的反应条件、绿色的水溶剂和广泛的底物适用性，使得该水相偶联策略具有重要的意义.

关键词： 铜; Ullmann反应; 糖基配体; 水

本文引用格式

刘学民 , 陈雯 , 倪邦庆 , 陈新志 , 钱超 , 葛新 . 糖基配体促进的铜催化水相Ullmann型C-N偶联反应[J]. 有机化学, 2018 , 38(7) : 1703 -1711 . DOI: 10.6023/cjoc201801031

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

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