Electrochemical Dehydrogenative sp2-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif

Electrochemical Dehydrogenative sp2-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 sp2-coupling was carried out by flow electrolysis. T...

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Hauptverfasser: Buchholz, Julian, Oehl, Elisabeth K, Hielscher, Maximilian M, Kuhn, Simone L, Schollmeyer, Dieter, Waldvogel, Siegfried R
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container_title Organic letters
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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 sp2-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.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 sp2-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 sp2-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif
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