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2020 , Vol. 40 >Issue 6: 1673 - 1679

DOI: https://doi.org/10.6023/cjoc201912038

研究论文

二苯甲酮腙与芳基氯化物及芳基硼酸的碳氮键偶联反应

  • 姚丹丹 ,
  • 张金利 ,
  • 徐亮
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  • 石河子大学化学化工学院 新疆兵团化工绿色过程重点实验室 新疆石河子 832003

收稿日期: 2019-12-26

  修回日期: 2020-02-21

  网络出版日期: 2020-03-06

基金资助

国家自然科学基金（Nos.21603150，21963010）资助项目.

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C—N Coupling Reactions between Benzophenone Hydrazone and Aryl Chlorides and Boronic Acids

  • Yao Dandan ,
  • Zhang Jinli ,
  • Xu Liang
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  • Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi, Xinjiang 832003

Received date: 2019-12-26

  Revised date: 2020-02-21

  Online published: 2020-03-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21603150, 21963010).

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摘要

钯催化的芳基卤化物与N-亲核试剂的Buchwald-Hartwig反应以及铜催化的芳基硼酸与N-亲核试剂的Chan-Evans-Lam反应都是构建C-N键的有效方法.在醋酸钯/叔丁醇体系或醋酸铜/二氯甲烷体系中，芳基氯化物或芳基硼酸分别与二苯甲酮腙反应构筑C-N键，生成相应的芳基腙，芳基腙水解之后可得到芳基肼.该类反应提供了一条利用低毒性的化学试剂合成芳基肼的间接路径.

关键词： Buchwald-Hartwig反应; Chan-Evans-Lam反应; 芳基硼酸; 二苯甲酮腙

本文引用格式

姚丹丹 , 张金利 , 徐亮 . 二苯甲酮腙与芳基氯化物及芳基硼酸的碳氮键偶联反应[J]. 有机化学, 2020 , 40(6) : 1673 -1679 . DOI: 10.6023/cjoc201912038

Abstract

Palladium catalyzed Buchwald-Hartwig reactions between aryl halides and N-nucleophiles, and the copper catalyzed Chan-Evans-Lam reactions between aryl boronic acids and N-nucleophiles are all effective methods for constructing C-N bonds. Herein, under palladium acetate/tert-butanol system or copper acetate/dichloromethane system, benzophenone hydrazone can react with aryl chlorides and aryl boronic acids to afford corresponding aryl hydrazones, respectively. The obtained products are easily hydrolyzed to form aryl hydrazines, thus providing an indirect pathway to access aryl hydrazines from relatively less toxic reagents.

Key words： Buchwald-Hartwig reaction; Chan-Evans-Lam reaction; aryl boronic acid; benzophenone hydrazone

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