Electrochemical Dehydrogenative sp 2 -Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif

A novel polycyclic naphthalenone motif was obtained by electrochemical synthesis starting from naphthols. The process is solvent controlled, and the highly diastereoselective cyclization is due to a solvent cage. The direct, anodic dehydrogenative sp -coupling was carried out by flow electrolysis. T...

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Veröffentlicht in:Organic letters 2024-12
Hauptverfasser: Buchholz, Julian, Oehl, Elisabeth K, Hielscher, Maximilian M, Kuhn, Simone L, Schollmeyer, Dieter, Waldvogel, Siegfried R
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Sprache:eng
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Zusammenfassung:A novel polycyclic naphthalenone motif was obtained by electrochemical synthesis starting from naphthols. The process is solvent controlled, and the highly diastereoselective cyclization is due to a solvent cage. The direct, anodic dehydrogenative sp -coupling was carried out by flow electrolysis. Ten derivatives containing this motif were synthesized in yields up to 88%, resulting in novel polycycles structurally similar to bioactive compounds like Daldionin, potentially exploring the bioactive profile.
ISSN:1523-7052