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Palladium anionic complexes with imidazolinium cations containing hydroxyl substituents were used as catalyst precursors in the Suzuki–Miyaura and the Heck cross-coupling. High activity of anionic complexes was noted in the Suzuki–Miyaura reaction of 2-bromotoluene with phenylboronic acid at 40  o C in 2-propanol and a 2-propanol/water mixture using conventional heating or microwaves. Similarly, bromonaphtalene and iodonaphtalene reacted efficiently with naphtylboronic acid and 4-methylnaphtylboronic acid. A remarkably lower activity was noted when anionic palladium complexes were employed in the Heck coupling of 2,3-dihydrofuran with iodobenzene. An increase in conversion in the Heck reaction was achieved when Pd(OAc) 2 was used as a catalyst precursor together with imidazolinium salts as co-catalysts.

Effect of imidazolinium salts bearing hydroxy substituents on palladium-catalysed Suzuki–Miyaura and Heck coupling reactions