有机化学 ›› 2019, Vol. 39 ›› Issue (10): 2906-2911.DOI: 10.6023/cjoc201904036 上一篇    下一篇

研究论文

氧鎓离子活化的烯丙基醚原位氧化/脱羧芳构化串联反应:一种合成N-烷基吡咯的新方法

李旭彬a, 周晨a, 刘星彤a, 王腾b, 虞心红a*(), 马红梅a*(), 李翠清b*()   

  1. a 华东理工大学药学院制药工程系 制药工程与过程化学教育部工程研究中心 上海市新药设计重点实验室生物反应器工程国家重点实验室 上海 200237
    b 北京石油化工学院 化学工程学院 北京 102617
  • 收稿日期:2019-04-13 修回日期:2019-05-07 出版日期:2019-10-25 发布日期:2019-05-28
  • 通讯作者: 虞心红,马红梅,李翠清 E-mail:xhyu@ecust.edu.cn;hmma@ecust.edu.cn;licuiqing@bipt.edu.cn
  • 基金资助:
    国家自然科学基金(21476078);上海市科学技术委员会(No. 12431900902)

ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles

Li, Xubina, Zhou, Chena, Liu, Xingtonga, Wang, Tengb, Yu, Xinhonga*(), Ma, Hongmeia*(), Li, Cuiqingb*()   

  1. a Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, Shanghai Key Laboratory of New Drug Design, State Key Laboratory of Bioengineering Reactors, School of Pharmacy,East China University of Science & Technology, Shanghai 200237;
    b College of Chemical Engineering, Beijing Institute of Petrochemical Technology, Beijing 102617
  • Received:2019-04-13 Revised:2019-05-07 Online:2019-10-25 Published:2019-05-28
  • Contact: Yu, Xinhong,Ma, Hongmei,Li, Cuiqing E-mail:xhyu@ecust.edu.cn;hmma@ecust.edu.cn;licuiqing@bipt.edu.cn
  • Supported by:
    Project supported by the National Natural Science Foundation of China(21476078);the Science and Technology Commission of Shanghai Municipality(No. 12431900902)

发展了一种氧鎓离子活化的烯丙基醚原位氧化/脱羧芳构化串联反应合成N-烷基吡咯化合物的新方法. 该反应涉及C—N键的形成和C—O键的断裂, 为制备N-烷基吡咯提供了新途径, 收率为29%~71%, 具有较好的官能团耐受性.

关键词: 醚氧化, 芳构化, 吡咯, 合成方法

An ipso-oxidation of allyl ether/decarboxylative aromatization cascade strategy is reported, resulting in the formation of N-alkyl pyrroles via oxocarbenium activation. This transformation, which involves formation of C—N bond and cleavage of C—O bond, provides a novel protocol that furnishes N-alkyl pyrroles in 29%~71% yields with good functional group tolerance.

Key words: oxidation of ether, aromatization, pyrroles, synthetic methods