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Chinese Journal of Organic Chemistry >

2017 , Vol. 37 >Issue 10: 2590 - 2608

DOI: https://doi.org/10.6023/cjoc201702041

REVIEW

Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes

  • Wang Ao ,
  • Xiao Yonglong ,
  • Zhou Yu ,
  • Xu Jinyi ,
  • Liu Hong
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  • a State Key Laboratory of Natural Medicines and Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210000;
    b CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203

Received date: 2017-02-26

  Revised date: 2017-05-25

  Online published: 2017-06-02

Supported by

Project supported by the National Natural Science Foundation of China (No.21632008).

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Abstract

Since the first stable N-heterocyclic carbene was isolated by Arduengo in 1991, N-heterocyclic carbine has developed rapidly as a kind of efficient organic catalyst. It plays important role in building complex molecules in organic synthesis for the characteristics of umpolung. Some special Lewis bases and oxidants can induce carbine reaction with carbonyl to form Breslow intermediates, enol and homoenolate, which expand the reaction greatly. In this paper, the recent progresses in organic catalytic reactions including Stetter reaction, a3-d3 umpolung catalyzed by carbines are reviewed.

Key words： N-heterocyclic carbene; organic catalytic; umpolung

Cite this article

Wang Ao , Xiao Yonglong , Zhou Yu , Xu Jinyi , Liu Hong . Progress of Organic Reactions Catalyzed by N-Heterocyclic Carbenes[J]. Chinese Journal of Organic Chemistry, 2017 , 37(10) : 2590 -2608 . DOI: 10.6023/cjoc201702041

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