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

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 2025-01, Vol.27 (1), p.25-29
Hauptverfasser: Buchholz, Julian, Oehl, Elisabeth K, Hielscher, Maximilian M, Kuhn, Simone L, Schollmeyer, Dieter, Waldvogel, Siegfried R
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container_issue 1
container_start_page 25
container_title Organic letters
container_volume 27
creator Buchholz, Julian
Oehl, Elisabeth K
Hielscher, Maximilian M
Kuhn, Simone L
Schollmeyer, Dieter
Waldvogel, Siegfried R
description 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.
doi_str_mv 10.1021/acs.orglett.4c03518
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title Electrochemical Dehydrogenative sp 2 -Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif
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