A novel acenaphthoimidazolyidene oxazolinic palladium complex and its efficient catalysis in Suzuki–Miyaura cross-coupling reactions of N-acyl-glutarimides via N–C cleavage†

Abstract

Herein, we synthesized a new Pd–N-heterocyclic carbene (Pd–NHC) complex that featured an acenaphthoimidazolylidene (AnIm) skeleton and 2-phenyl-2-oxazoline. This catalyst exhibited extremely high efficiency in Suzuki–Miyaura couplings between N-acyl-glutarimides and organoboronic acids, affording various aryl ketones in excellent yields with a broad substrate scope and wide functional group compatibility. Notably, the reactions were completed in just 5 hours with only 0.5 mol% of catalyst. In addition, this catalytic system also enables the efficient synthesis of functional molecular intermediates. The catalyst, designed through the synergistic integration of a throw-away ligand and an extended conjugated NHC system, further demonstrates its remarkable potential.