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2019 , Vol. 39 >Issue 10: 2906 - 2911

DOI: https://doi.org/10.6023/cjoc201904036

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 ,
  • 周晨 ,
  • 刘星彤 ,
  • 王腾 ,
  • 虞心红 ,
  • 马红梅 ,
  • 李翠清
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  • 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

  网络出版日期: 2019-05-28

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)

收起

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

  • Xubin Li, ,
  • Chen Zhou, ,
  • Xingtong Liu, ,
  • Teng Wang, ,
  • Xinhong Yu, ,
  • Hongmei Ma, ,
  • Cuiqing Li,
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  • 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 date: 2019-04-13

  Revised date: 2019-05-07

  Online published: 2019-05-28

Supported by

Project supported by the National Natural Science Foundation of China(21476078);the Science and Technology Commission of Shanghai Municipality(No. 12431900902)

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摘要

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

本文引用格式

李旭彬 , 周晨 , 刘星彤 , 王腾 , 虞心红 , 马红梅 , 李翠清 . 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[J]. 有机化学, 2019 , 39(10) : 2906 -2911 . DOI: 10.6023/cjoc201904036

Abstract

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

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