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

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-10 DOI:10.1021/acs.orglett.4c03518

Julian Buchholz, Elisabeth K. Oehl, Maximilian M. Hielscher, Simone L. Kuhn, Dieter Schollmeyer, Siegfried R. Waldvogel

引用次数: 0

Abstract

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.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.