有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2166-2174.DOI: 10.6023/cjoc201905050 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

研究论文

咔唑基高价碘试剂参与的活化芳烃直接咔唑化反应研究

兰天磊a,b, 张越a,b, 刘伟c, 席婵娟a, 陈超a   

  1. a 清华大学化学系 生命有机磷化学及化学生物学教育部重点实验室 北京 100084;
    b 天津科技大学化工与材料学院 天津 300457;
    c 天津科技大学理学院 天津 300457
  • 收稿日期:2019-05-28 修回日期:2019-07-12 出版日期:2019-08-25 发布日期:2019-07-17
  • 通讯作者: 陈超 E-mail:chenchao01@mails.tsinghua.edu.cn
  • 基金资助:

    国家重点研发计划(No.2016YFB0401400)、国家自然科学基金(Nos.21302139,21672120,21871158)和霍英东青年教师基金(No.151014)资助项目.

Carbazolation Study of Active Arenes with Carbazole-Containing Hypervalent Iodine(III) Reagents

Lan Tianleia,b, Zhang Yuea,b, Liu Weic, Xi Chanjuana, Chen Chaoa   

  1. a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084;
    b College of Chemical Engineering and Materials Science, Tianjin University of Science & Technology, Tianjin 300457;
    c College of Sciences, Tianjin University of Science & Technology, Tianjin 300457
  • Received:2019-05-28 Revised:2019-07-12 Online:2019-08-25 Published:2019-07-17
  • Contact: 10.6023/cjoc201905050 E-mail:chenchao01@mails.tsinghua.edu.cn
  • Supported by:

    Project supported by the National Key Research and Development Program of China (No. 2016YFB0401400), the National Natural Science Foundation of China (Nos. 21302139, 21672120, 21871158) and the Fok Ying Tong Education Foundation of China (No. 151014).

咔唑及其衍生物在医药和光电材料领域有着广泛的应用.合成了一种稳定的含有咔唑基团的环状高价碘试剂,该试剂属于苯并碘氧杂环类化合物,在Cu(I)催化条件下可以与芳烃底物反应,得到N-芳基咔唑衍生物,反应条件温和,适用于多种富电子芳烃,并提出了一个可能的自由基反应机理.

关键词: 咔唑, 高价碘试剂, N-芳基化, 铜催化

Carbazole and its derivatives are widely used in the field of medicine and photoelectric materials. A kind of stable cyclic hypervalent iodine reagents containing carbazole group was developed, which belong to benziodoxole compounds. In the presence of Cu(I) catalyst, these reagents reacted with aromatic substrates to give N-aryl carbazole derivatives. The reaction conditions are mild and suitable for a variety of electron-rich arenes. And a radical mechanism was proposed.

Key words: carbazole, hypervalent iodine reagent, N-arylation, copper-catalysis