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

A series of new derivatives of N-(1-methylpyridin-4(1H)-ylidene)amines, [L1]-[L5], 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 triflate 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(1H)-ylidene)amine ligands considerably improve the catalytic activity of palladium acetate towards Heck-Mizoroki carbon-carbon cross-coupling reactions.