Photoredox Catalyzed Conia-Ene-Type Cyclization/Smiles Rearrangement Cascade Reactions to Access Substituted Methylenecarbocycles

We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methyleneca...

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Veröffentlicht in:Organic letters 2024-09, Vol.26 (37), p.7971-7975
Hauptverfasser: Zhang, Keyuan, Jiang, Qi, He, Chonglong, Hu, Mingyou, Cheng, Yangyang, Duan, Xin-Hua, Liu, Le
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Sprache:eng
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Zusammenfassung:We report a novel visible-light-driven photoredox-catalyzed cascade reaction involving Conia-ene-type cyclization and Smiles rearrangement initiated from alkyne-tethered α-sulfonyl esters. This methodology not only facilitates the rapid synthesis of a broad spectrum of highly substituted methylenecarbocycles but also introduces a new mechanistic pathway with aryl group migration, surpassing the conventional 1,5-hydrogen shift typically observed in Conia-ene reactions.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03033