Photoredox-Catalyzed Divergent Radical Cascade Annulations of 1,6-Enynes via Pyridine N‑Oxide-Promoted Vinyl Radical Generation

The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1,6-enynes were developed. A series of cyclopropane-fused hetero- and carbo-bicyclic, tricyclic, and spiro-tetracyclic compounds were facilely synthesized from a broad scope of 1,6-enynes and 2,6-lutidine N-oxide under...

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Bibliographic Details
Published in:Organic letters 2023-12, Vol.25 (51), p.9219-9224
Main Authors: Wang, Ban, Singh, Jujhar, Deng, Yongming
Format: Article
Language:English
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Summary:The divergent organophotoredox-catalyzed radical cascade annulation reactions of 1,6-enynes were developed. A series of cyclopropane-fused hetero- and carbo-bicyclic, tricyclic, and spiro-tetracyclic compounds were facilely synthesized from a broad scope of 1,6-enynes and 2,6-lutidine N-oxide under mild and metal-free conditions with blue light-emitting diode light irradiation. The cascade annulation reaction occurs with the intermediacy of a β-oxyvinyl radical, which is produced from photocatalytically generated pyridine N-oxy radical addition to the carbon–carbon triple bond.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03930