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One-pot synthesis of new N -(1-methylpyridin-4(1H)-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. | Turkish Journal of Chemistry Turk J Chem 2018 42 63 74 http journals.tubitak.gov.tr chem ITAK c TUB Research Article doi 10.3906 kim-1703-44 One-pot synthesis of new N - 1-methylpyridin-4 1H -ylidene amine ligands for palladium-catalyzed Heck coupling reaction Muhammad ZAFAR1 Sabeen ZAHRA2 Muhammad TAHIR3 Ehsan MUGHAL2 Muhammad NAZAR2 Hummera RAFIQUE2 1 Department of Chemistry Quaid-i-Azam University Islamabad Pakistan 2 Department of Chemistry University of Gujrat Gujrat Pakistan 3 Department of Physics University of Sargodha Sargodha Pakistan Received 16.03.2017 Accepted Published Online 13.08.2017 Final Version 08.02.2018 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 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 1 H -ylidene amine ligands considerably improve the catalytic activity of palladium acetate towards Heck Mizoroki carbon carbon cross-coupling reactions. Key words N - 1-Methylpyridin-4 1 H -ylidene amines pyridinium amido Heck Mizoroki 1. Introduction Phosphines and N-heterocyclic carbenes NHCs have gained an enormous reputation in the homogeneous cat- alytic world owing to their extensive utility in chemical transformations. 1 N - 1-Methylpyridin-4 1H -ylidene amine PYE as a ligand has been found to have properties comparable with these versatile ligands due to the exceptional electron donor ability towards metals in a coordination compound. 2 In addition steric properties of PYE around metal can be altered by synthesizing various libraries of its derivatives. 3 It can resonate between zwitterion pyridinium amido and neutral N - 1-methylpyridin-4