萘酚的电化学脱氢sp-偶联反应构建多环萘醌骨架
Electrochemical Dehydrogenative sp-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif.
作者信息
Buchholz Julian, Oehl Elisabeth K, Hielscher Maximilian M, Kuhn Simone L, Schollmeyer Dieter, Waldvogel Siegfried R
机构信息
Max-Planck-Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470 Mülheim an der Ruhr, Germany.
Department of Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128 Mainz, Germany.
出版信息
Org Lett. 2025 Jan 10;27(1):25-29. doi: 10.1021/acs.orglett.4c03518. Epub 2024 Dec 10.
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.
通过从萘酚开始的电化学合成获得了一种新型的多环萘醌基序。该过程受溶剂控制，高度非对映选择性环化归因于溶剂笼。通过流动电解进行直接的阳极脱氢sp偶联。合成了十种含有该基序的衍生物，产率高达88%，得到了结构上类似于生物活性化合物如达尔多宁的新型多环化合物，可能探索其生物活性特征。
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