Chinese Journal of Organic Chemistry >
Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines
Received date: 2024-01-29
Revised date: 2024-03-19
Online published: 2024-04-10
Supported by
Scientific Research Foundation of Hunan Provincial Education Department(23B0650); Natural Science Foundation of Hunan Province(2022JJ30418); Key Scientific Research Foundation of Hunan University of Arts and Science(22ZD04); Innovation and Entrepreneurship Training Program for College Students of Hunan University of Arts and Science(XDC202318)
An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide (TMSN3) has been developed using organic dye Rose Bengal as the photocatalyst. This method did not require metal catalysts and additives, and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields. Mechanistic studies demonstrated that the reaction proceeded via a radical pathway.
Yucai Tang , Yupeng He , Biyu Yang , Jinglin Duan , Changyuan Du , Jie Jiang , Jiali Li , Ruohan Pan , Yu Chen , Xuewen Liu . Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2286 -2295 . DOI: 10.6023/cjoc202401034
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