Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (10): 2059-2066.DOI: 10.6023/cjoc201505009 Previous Articles     Next Articles



张文生a, 许文静a, 匡春香b   

  1. a 焦作师范高等专科学校理工学院 焦作 454001;
    b 同济大学化学系 上海 200092
  • 收稿日期:2015-05-06 修回日期:2015-06-02 发布日期:2015-06-16
  • 通讯作者: 张文生
  • 基金资助:

    国家自然科学基金(No. 21272174)、河南省自然科学基金(No. 142300410338)、河南省教育厅自然科学重点研究计划(No. 14B150056)和焦作市科学技术局科技计划(No. 2014400038)资助项目.

Research Progress on Multicomponent Reactions of Sulfonyl Azides and Terminal Alkynes

Zhang Wenshenga, Xu Wenjinga, Kuang Chunxiangb   

  1. a School of Technology, Jiaozuo Teachers College, Jiaozuo 454001;
    b Department of Chemistry, Tongji University, Shanghai 200092
  • Received:2015-05-06 Revised:2015-06-02 Published:2015-06-16
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272174), the Foundation of He'nan Scientific and Technological Committee (No. 142300410338), the Science and Technology Research Key Program of Henan Educational Committee (No. 14B150056) and the Foundation of Jiaozuo Scientific and Technological Bureau (No. 2014400038).

In recent years, the copper-catalyzed multicomponent reactions involving sulfonyl azides and terminal alkynes have received much attention in organic chemistry. N-Sulfonyl ketenimine intermediates, generated in situ from the copper(I)-catalyzed cycloaddition of sulfonyl azides and terminal alkynes, could be trapped by various nucleophiles such as amines, alcohols and H2O, etc. In addition, the ketenimine intermediates could also react with a wide range of olefins though [2+2], [3+2] and [4+2] cycloadditions. Moreover, attack of the ketenimine by intramolecular nucleophilic functional group and the following rearrangement or σ-shift course have become a powerful tool for the construction of diverse biologically and pharmacologically active heterocyclic compounds. In this paper, the research achievements recently in the important area are described.

Key words: sulfonyl azide, alkyne, ketenimine, multicomponent reaction, copper-catalyzed