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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 3: 1207 - 1215

DOI: https://doi.org/10.6023/cjoc202009020

ARTICLES

Copper-Catalyzed C—H Bond and N—H Bond Insertion Reaction Based on Azide-Ynamide Cyclization

  • Xiaotao Liu ,
  • Xin Liu ,
  • Longwu Ye
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  • a Wanxiang Technology Co., Ltd., Huaian, Jiangsu 223300
    b College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005
    c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry,Chinese Academy of Sciences, Shanghai 200032
* Corresponding authors. E-mail: ;

Received date: 2020-09-08

  Revised date: 2020-10-02

  Online published: 2020-10-28

Supported by

National Natural Science Foundation of China(21772161)

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Abstract

A copper-catalyzed azide-ynamide cyclization to synthesize isoquinoline derivatives is reported. First, α-imino copper carbene intermediate is generated via Cu(I)-catalyzed azide-ynamide cyclization, then this copper carbene can be captured by indoles and anilines to form C—H and N—H insertion products. The notable advantages of this method include a simple procedure, mild reaction conditions and widespread availability of the substrates. Thus, this protocol provides a highly convenient and efficient route for the preparation of natural products and active molecules which contain the isoquinoline-indole or isoquinoline-aniline skeletons.

Key words： cyclization reaction; copper catalysis; copper carbenes; ynamides

Cite this article

Xiaotao Liu , Xin Liu , Longwu Ye . Copper-Catalyzed C—H Bond and N—H Bond Insertion Reaction Based on Azide-Ynamide Cyclization[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 1207 -1215 . DOI: 10.6023/cjoc202009020

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