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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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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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

Cite this article

Xubin Li, , Chen Zhou, , Xingtong Liu, , Teng Wang, , Xinhong Yu, , Hongmei Ma, , Cuiqing Li, . ipso-Oxidation of Allyl Ether/Decarboxylative Aromatization Cascade Strategy via Oxocarbenium Activation: A Novel Approach for Synthesis of N-Alkyl Pyrroles[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2906 -2911 . DOI: 10.6023/cjoc201904036

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