Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity

A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3‐methyl‐1‐(2′‐phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH]PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h–1 have been reached with catalyst concentrations as low as 0.01 mol‐%. A cationic phthalimido‐functionalized N‐heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki–Miyaura cross‐coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h–1, were achieved with 0.01 mol‐% of the complex.