Iron Catalyzed Dearomatization of Pyridines into Annelated Azepine Derivatives in a One-Step, Three-Component Reaction

Commercially available Fe­(TTP)Cl catalyzes three-component dearomative formal cycloaddition reactions between pyridines, diazo compounds, and coumalates. Diversely substituted annelated seven-membered N-heterocycles could be generated in less than 10 min in one step at room temperature. The reactio...

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Bibliographic Details
Published in:Organic letters 2023-01, Vol.25 (1), p.256-260
Main Authors: Mamontov, Alexander, Chang, Liang, Dossmann, Héloïse, Bertrand, Benoît, Dechoux, Luc, Thorimbert, Serge
Format: Article
Language:English
Subjects:
Catalysis
Chemical Sciences
Organic chemistry
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Summary:Commercially available Fe­(TTP)Cl catalyzes three-component dearomative formal cycloaddition reactions between pyridines, diazo compounds, and coumalates. Diversely substituted annelated seven-membered N-heterocycles could be generated in less than 10 min in one step at room temperature. The reaction is compatible to gram scale. The extension to benzimidazoles in place of pyridines has been successfully demonstrated. The mechanism of this reaction has been carefully examined by computational studies that corroborate the observed regioselectivities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04088