Potassium base-catalyzed redox isomerization of propargylic alcohols to chalcones

Abstract

Chalcone derivatives are frequently found in bioactive compounds, natural products, and pharmaceuticals. In this study, we developed a KO^tBu/DMF catalytic system to efficiently synthesize chalcone derivatives by isomerizing propargylic alcohols bearing aryl substituents at the 1- and 3-positions. Mechanistic investigations confirmed that a 1,3-hydride shift was the key process for the successful reaction. Our method does not involve the use of transition metals and possesses economic and environmental benefits.

Graphical Abstract

Keywords:

• Chalcones
• isomerization
• potassium
• propargylic alcohols

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the Endo Saijiro Memorial Foundation for Science and Technology.