可见光催化炔烃串联氰基烷基磺酰化/环化  

Visible-Light-Catalyzed Tandem Cyanoalkylsulfonylation/Cyclization of Alkynes

作　　者：刘宇[1,2] 陈赞 陈镤 熊碧权[1] 谢军 刘岸 梁云[2] 唐课文[1] Liu Yu;Chen Zan;Chen Pu;Xiong Biquan;Xie Jun;Liu An;Liang Yun;Tang Kewen(Department of Chemistry and Chemical Engineering,Hunan Institute of Science and Technology,Yueyang,Hunan 414006;Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province,Hunan Normal University,Changsha 410081)

机构地区：[1]湖南理工学院化学化工学院,湖南岳阳414006 [2]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

出　　处：《有机化学》2021年第6期2290-2301,共12页Chinese Journal of Organic Chemistry

基　　金：Project supported by the National Natural Science Foundation of China(Nos.22078084,51874132);the Scientific Research Fund of Hunan Provincial Education Department(Nos.20A224,20A213,18B355);the Science and Technology Planning Project of Hunan Province(Nos.2020RC3056,2018TP1017);the Natural Science Foundation of Hunan Province(Nos.2020JJ5221,2020JJ5212)。

摘　　要：报道了一种在无过渡金属条件下可见光催化炔烃与环酮肟衍生物的串联氰基烷基磺酰化/环化反应,通过SO_(2)的插入合成2-氰基烷基磺酰基-9H-吡咯并[1,2-a]吲哚.该碳碳叁键的双官能团化包括自由基机理,依次经历了亚胺自由基的形成、环酮的开环、SO_(2)的插入、磺酰基对碳碳叁键的加成、分子内环化和异构化.A transition-metal-free visible-light-mediated tandem cyanoalkylsulfonylation/cyclization of alkynes with cycloketone oxime derivatives for the construction of 2-cyanoalkylsulfonyl-9 H-pyrrolo[1,2-a]indoles through the insertion of SO_(2) 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 SO_(2),addition of sulfonyl radical to carbon-carbon triple bonds,intramolecular cyclization and isomerization.

关 键 词：可见光催化 SO_(2)插入 环酮肟酯 N-炔丙基吲哚 

分 类 号：O621.251[理学—有机化学]