Cyclopalladated Arylimine Self-Assembly Films for Suzuki Reaction

A series of cyclopalladated arylimine self‐assembly films were prepared through chemical grafting to substrates and used to catalyze a Suzuki coupling reaction. Atomic force microscopy, water contact angle analysis, cyclic voltammetry, scanning electron microscopy, attenuated total‐reflectance infrared, and X‐ray photoelectron spectroscopy were used to analyze the morphology and composition of the heterogeneous catalysts. The results show that these cyclopalladated arylimine self‐assembly films immobilized on substrates could be used as efficient and reusable heterogeneous catalysts in the Suzuki reaction of aryl bromides under open air conditions in aqueous solution. These catalysts exhibited 10 times the catalytic performance of the homogeneous counterpart. The palladium catalysts were grafted onto the internal surface of the round‐bottomed flasks. The reaction flasks acted as both reaction vessels and catalysts, which simplified the reaction operations. The catalysts were run over 8 cycles without showing any sign of deactivation, suggesting the potential of the catalysts as advanced functional materials with applications in the heterogeneous catalysis of Suzuki reactions. Cyclos and cycles: Cyclopalladated arylimine complexes are immobilized on solid slides and characterized. The heterogeneous catalyst obtained exhibits 10 times the catalytic performance of its homogeneous counterpart. None of the reactions require the use of ligands, air isolation, or assistant solvents. The catalysts are run for 8 cycles without deactivation. A Suzuki reaction mechanism is proposed.