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2013 , Vol. 33 >Issue 04: 840 - 847

DOI: https://doi.org/10.6023/cjoc201301067

研究论文

CuI催化的酚与富电子对溴苯甲醚和缺电子间溴苯甲醚的O-芳基化反应研究

  • 杏朝刚 ,
  • 俞建忠 ,
  • 张培志 ,
  • 吴军
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  • a 浙江大学化学系 杭州 310027;
    b 浙江科技学院生物与化学工程学院 杭州 310012

收稿日期: 2013-01-25

  修回日期: 2013-02-27

  网络出版日期: 2013-03-01

基金资助

国家自然科学基金(No. 31071720)和浙江省自然科学基金(No. D3080282 )资助项目.

收起

CuI-Catalyzed O-Arylation of Phenols with Electron-Rich 4-Bromoanisole and Electron-Deficient 3-Bromoanisole

  • Xing Chaogang ,
  • Yu Jianzhong ,
  • Zhang Peizhi ,
  • Wu Jun
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  • a Department of Chemistry, Zhejiang University, Hangzhou 310027;
    b School of Biological and Chemistry Engineering, Zhejiang University of Science and Technology, Hangzhou 310012

Received date: 2013-01-25

  Revised date: 2013-02-27

  Online published: 2013-03-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 31071720) and the Natural Science Foundation of Zhejiang Province (No. D3080282).

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摘要

报道碘化亚铜催化的酚与富电子的对溴苯甲醚与缺电子的间溴苯甲醚的O-芳基化反应. 研究发现缺电子的间溴苯甲醚在反应时表现出更高的反应活性, 而富电子的对溴苯甲醚反应活性较低. 通过提高反应温度和延长反应时间可使对溴苯甲醚发生O-芳基化反应, 产物的收率和缺电子的间溴苯甲醚相当. 用此方法成功合成了4-(4-氯苯氧基)苯甲醚, 并进一步合成了除草剂Clofop.

关键词： 交叉偶联; 富电子; 缺电子; CuI催化; O-芳基化

本文引用格式

杏朝刚 , 俞建忠 , 张培志 , 吴军 . CuI催化的酚与富电子对溴苯甲醚和缺电子间溴苯甲醚的O-芳基化反应研究[J]. 有机化学, 2013 , 33(04) : 840 -847 . DOI: 10.6023/cjoc201301067

Abstract

CuI-catalyzed O-arylation of phenols with electron-rich 4-bromoanisole and electron-deficient 3-bromoanisole was described. Electron-deficient 3-bromoanisole showed high reactivity, and electron-rich 4-bromoanisole had low reactivity. O-Arylation of 4-bromoanisole occurred to afford the product by increasing reaction temperature and time. This reaction was applied to the synthesis of 1-chloro-4-(4-methoxyphenoxy)benzene, which was further synthesized to herbicide Clofop.

Key words： cross-coupling; electron-rich; electron-deficient; CuI-catalyzed; O-arylation

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