Palladium/1,3-bis(ferrocenylmethyl)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions
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Date
2023
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Abstract
We describe here the first results on the catalytic performance of in-situ prepared [Pd(O2CCH3)2] / 1,3-bis(ferrocenylmethyl)imidazolinium chloride. This saturated imidazole ring was successfully used in Suzuki cross-coupling reactions of various aryl bromides (bromobenzene, 2-bromobenzonitrile, 2-bromotoluene, p-bromobenzaldehyde, p-bromoacetophenone, p-bromoanisole, p-bromotoluene, and p-bromobenzotrifluoride) with phenylboronic acid under optimal conditions. The optimal conditions were determined to be 24 hours, 80°C, K2CO3 as a base, dioxane as a solvent, and 1,3-bis(ferrocenylmethyl)imidazolinium chloride as an auxiliary ligand. Under these conditions, 2-bromobenzonitrile, p-bromoacetophenone, and p-bromobenzaldehyde reacted with phenylboronic acid in moderate yields of 57%, 50%, and 46%, respectively. Catalytic experiments showed that the [Pd(O2CCH3)2] / 1,3-bis(ferrocenylmethyl)imidazolinium chloride catalytic system was moderately efficient in the Suzuki cross-coupling reaction of aryl bromides in dioxane.