Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1207-1215.DOI: 10.6023/cjoc202009020 Previous Articles     Next Articles

ARTICLES

基于叠氮-炔酰胺环化的铜催化碳氢键和氮氢键插入反应研究

刘晓涛a,*(), 刘鑫b, 叶龙武b,c,*()   

  1. a 万香科技股份有限公司 江苏淮安 223300
    b 厦门大学化学化工学院 福建厦门 361005
    c 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032
  • 收稿日期:2020-09-08 修回日期:2020-10-02 发布日期:2020-10-28
  • 通讯作者: 刘晓涛, 叶龙武
  • 基金资助:
    国家自然科学基金(21272191)

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

Xiaotao Liua,*(), Xin Liub, Longwu Yeb,c,*()   

  1. 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
  • Received:2020-09-08 Revised:2020-10-02 Published:2020-10-28
  • Contact: Xiaotao Liu, Longwu Ye
  • About author:
    * Corresponding authors. E-mail: ;
  • Supported by:
    National Natural Science Foundation of China(21772161)

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