Synthesis of Imidazole-Based Functionalized Mesoionic Carbene Complexes of Palladium: Comparison of Donor Properties and Catalytic Activity toward Suzuki–Miyaura Coupling

Abstract

Three different backbone-monofunctionalized imidazolium salts have been synthesized using the metal–halogen exchange procedure, and their corresponding mesoionic carbene complexes with palladium were prepared via oxidative addition without protection of the C2 position. The donor properties were evaluated with 31P NMR spectroscopy of the respective palladium complexes. The catalytic activity of these complexes toward Suzuki–Miyaura coupling of aryl bromides was also explored. Also, in one case, a comparison of donor properties was made with those of a “normal” carbene with similar steric bulk.