Synthesis of a New Surfactant-like Triazine-functionalized Ligand for Carbon-Carbon and Carbon-Heteroatom Bond Formations

Transition metal-catalyzed organic transformations are among the most important approaches in organic synthesis [1].In these reactions, the existence of an appreciate ligand is critical and many of the challenges in this field referred to the development of suitable ligands for fine chemical synthesis [2]. Triazine-based ligands have been considered as efficient ligands in transition-metal catalyzed organic reactions due to their many advantages in comparison with other ligands.There are some interesting reports in the literature on the use of 2,4,6-trichloro-1,3,5-triazine(TCT) in the synthesis of ligands for application in metalcatalyzed organic reactions. In fact, to synthesise these ligands, TCT was used as the starting material in order to generate a triazine moiety in the structure of an organic–inorganic hybrid material or polymer[3]. In the current study, our goal is to develop a novel catalytic system based on TCT and micellar concepts that enable the use of water as a solvent for the Pd-catalyzed coupling reactions. Our study was initiated by the synthesis of a surfactant-like triazinefunctionalizedligand using the reaction of 3 equivalents ofdodecan-1-amine with TCT. In the structure of the ligand, thetriazine ring provides the nitrogencenter of ligand and the dodecyl carbon chain participates inthe surfactant part. The synthetic ligandwas characterized using elemental analysis, 1HNMR and 13CNMR. Next, the synthesized pseudo surfactant triazinefunctionalized ligand was used in the carbon-carbon and carbon-heteroatom bond formation reactions.