Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2290-2301.DOI: 10.6023/cjoc202102051 Previous Articles     Next Articles

ARTICLES

可见光催化炔烃串联氰基烷基磺酰化/环化

刘宇a,b, 陈赞a, 陈镤a, 熊碧权a, 谢军a,*(), 刘岸a,*(), 梁云b, 唐课文a   

  1. a 湖南理工学院化学化工学院 湖南岳阳 414006
    b 湖南师范大学 湖南省有机功能分子组装与应用重点实验室 长沙 410081
  • 收稿日期:2021-02-27 修回日期:2021-03-18 发布日期:2021-03-25
  • 通讯作者: 谢军, 刘岸
  • 基金资助:
    国家自然科学基金(22078084); 国家自然科学基金(51874132); 湖南省教育厅科学研究基金(20A224); 湖南省教育厅科学研究基金(20A213); 湖南省教育厅科学研究基金(18B355); 湖南省科技计划项目(2020RC3056); 湖南省科技计划项目(2018TP1017); 湖南省自然科学基金(2020JJ5221); 湖南省自然科学基金(2020JJ5212)

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/ Cyclization of Alkynes

Yu Liua,b, Zan Chena, Pu Chena, Biquan Xionga, Jun Xiea(), An Liua(), Yun Liangb, Kewen Tanga   

  1. a Department of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang, Hunan 414006
    b Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081
  • Received:2021-02-27 Revised:2021-03-18 Published:2021-03-25
  • Contact: Jun Xie, An Liu
  • Supported by:
    National Natural Science Foundation of China(22078084); National Natural Science Foundation of China(51874132); Scientific Research Fund of Hunan Provincial Education Department(20A224); Scientific Research Fund of Hunan Provincial Education Department(20A213); Scientific Research Fund of Hunan Provincial Education Department(18B355); Science and Technology Planning Project of Hunan Province(2020RC3056); Science and Technology Planning Project of Hunan Province(2018TP1017); Natural Science Foundation of Hunan Province(2020JJ5221); Natural Science Foundation of Hunan Province(2020JJ5212)

A transition-metal-free visible-light-mediated tandem cyanoalkylsulfonylation/cyclization of alkynes with cycloketone oxime derivatives for the construction of 2-cyanoalkylsulfonyl-9H-pyrrolo[1,2-a]indoles through the insertion of SO2 is reported. The difunctionalization of carbon-carbon triple bonds includes a radical mechanism and undergoes the formation of iminyl radical, ring-opening of cycloketone, insertion of SO2, addition of sulfonyl radical to carbon-carbon triple bonds, intramolecular cyclization and isomerization.

Key words: visible-light-catalysis, the insertion of SO2, cycloketone oxime esters, N-propargylindoles