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

Adam Morel, Anna Trzeciak

Abstract

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 oC 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.

Keywords

ionic liquids; imidazolinium salts; palladium; Suzuki-Miyaura; Heck

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DOI

https://doi.org/10.17721/fujcV4I1P76-84

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