ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
A Potassium Base-Promoted Intramolecular Enolate-Olefin Metathesis.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Polycyclic aromatic hydrocarbons (PAHs) are important structures known for their unique properties. Herein, we present a transition-metal-free method for synthesizing hydroxy-substituted PAHs using base-promoted intramolecular enolate-olefin-metathesis chemistry. 2-Acyl-2'-alkenylbiaryl substrates were subjected to [2 + 2]-/retro-[2 + 2]-cycloaddition sequences to afford functionalized PAH derivatives, including enantiomerically enriched [7]helicenes. Density functional theory (DFT) calculations predicted that ionic and radical intermediates are involved in a stepwise process. Various biaryl substrates, including heteroatom-containing compounds, were successfully converted into the desired PAHs. The developed method also enabled the synthesis of π-extended arenols, thereby offering a sustainable and efficient alternative to transition-metal-catalyzed processes.
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