α, β-Alkynone Accelerated PPM Level Pd-Catalyzed Sonogashira Coupling Reaction

Abstract

In the palladium-catalyzed C−C coupling reaction, electron-rich phosphine ligands and a catalytic amount of catalyst loading are required in most cases. Herein, a bench-stable, easily modified and less toxic alkynone was utilized in palladium-catalyzed Sonogashira coupling to replace conventional phosphine ligands. With 1-(4-methoxyphenyl)-3-phenyl-2-yn-1-one (L2) as the ligand, catalyst loading was reduced to 5-10 ppm. In this newly developed catalytic system, a variety of (hetero)arene iodines and alkynes could be tolerated, resulting in good yields of the corresponding cross-coupling products.

Keywords

• <i>α</i>
• <i>β</i>-alkynone
• pd-catalyzed c−c coupling
• <i>π</i>-acidicity