Visible Light-Catalyzed Cascade Radical Cyclization of N‑Propargylindoles with Acyl Chlorides for the Synthesis of 2‑Acyl‑9H‑pyrrolo[1,2‑a]indoles
A novel and convenient visible light-catalyzed tandem radical cyclization of N-propargylindoles with acyl chlorides for accessing 2-acyl-9H-pyrrolo[1,2-a]indoles is established. This transformation involves sequential addition of the acyl radical to the carbon–carbon triple bond, intramolecular cy...
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Veröffentlicht in: | Journal of organic chemistry 2020-02, Vol.85 (4), p.2385-2394 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A novel and convenient visible light-catalyzed tandem radical cyclization of N-propargylindoles with acyl chlorides for accessing 2-acyl-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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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b03090 |