4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 4, Pages 2385-2394

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b03090

Keywords

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Funding

  1. Scientific Research Fund of Hunan Provincial Education Department [16A087, 18B350]
  2. Hunan Provincial Innovation Foundation For Postgraduate [CX20190921]
  3. Natural Science Foundation of Hunan Province [2018B3208]
  4. National Natural Science Foundation of China [21602056, 51874132]

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A novel and convenient visible light-catalyzed tandem radical cyclization of N-propargylindoles with acyl chlorides for accessing 2-aryl-9H-pyrrolo[1,2-a]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.

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