One-Pot Regio- and Diastereoselective Gold-Catalyzed Propargylation of in Situ Activated Chromones and Consecutive Cyclization

Herein, we report a gold-catalyzed propargylation of chromone derivatives by propargylsilanes. Chromones are synergistically activated by the silylium cation resulting from the gold activation of the propargylsilane. The reaction exclusively occurs at the C2-position of the chromone, and a single di...

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Bibliographic Details
Published in:Organic letters 2024-11, Vol.26 (49), p.10487-10492
Main Authors: Álvarez-Valle, Julio, Fernández, Sergio, Merino-Robledillo, Cecilia, Funes-Ardoiz, Ignacio, Sampedro, Diego, Santamaría, Javier
Format: Article
Language:English
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Letter
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Summary:Herein, we report a gold-catalyzed propargylation of chromone derivatives by propargylsilanes. Chromones are synergistically activated by the silylium cation resulting from the gold activation of the propargylsilane. The reaction exclusively occurs at the C2-position of the chromone, and a single diastereoisomer is formed. Computational studies performed on the reaction mechanism rationalize the formation of the preferred diastereoisomer. Finally, a dual consecutive cascade reaction based on different gold catalysts enables the formation of complex tricyclic compounds.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c03812