One-pot synthesis of new N -(1-methylpyridin-4(1 H ) -ylidene)amine ligands for palladium-catalyzed Heck coupling reaction

Abstract

A series of new derivatives of N -(1-methylpyridin-4(1 H )-ylidene)amines, [L 1 ]{[L 5 ], were synthesized and characterized by FTIR, NMR, MS, and XRD analysis. These targeted compounds were synthesized by the melt reaction between N -methylated-4-chloropyridinium tri ate and corresponding amines (1-naphthyl amine, o -ansidine, 2-nitroaniline, p-ansidine, and cyclohexyl amine) followed by the addition of sodium hydride in dichloromethane in the same pot. These highly electron-donating N -(1-methylpyridin-4(1 H )-ylidene)amine ligands considerably improve the catalytic activity of palladium acetate towards Heck{Mizoroki carbon{carbon cross-coupling reactions.