Visible Light-Catalyzed Cascade Radical Cyclization of N -Propargylindoles with Acyl Chlorides for the Synthesis of 2-Acyl-9 H -pyrrolo[1,2- a ]indoles

A novel and convenient visible light-catalyzed tandem radical cyclization of -propargylindoles with acyl chlorides for accessing 2-acyl-9 -pyrrolo[1,2- ]indoles is established. This transformation involves sequential addition of the acyl radical to the carbon-carbon triple bond, intramolecular cycli...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-02, Vol.85 (4), p.2385-2394
Main Authors: Liu, Yu, Chen, Zan, Wang, Qiao-Lin, Chen, Pu, Xie, Jun, Xiong, Bi-Quan, Zhang, Pan-Liang, Tang, Ke-Wen
Format: Article
Language:English
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Summary:A novel and convenient visible light-catalyzed tandem radical cyclization of -propargylindoles with acyl chlorides for accessing 2-acyl-9 -pyrrolo[1,2- ]indoles is established. This transformation involves sequential addition of the acyl radical to the carbon-carbon triple bond, intramolecular cyclization with the 2-position of indole, and isomerization of the carbon-carbon double bond. The experimental results show that this reaction contains a radical pathway and a radical chain process is not the major pathway for the formation of products.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03090