Abstract
AbstractThe palladium(II) complexes, PdCl2(cod) (1), PdCl2[P(OPh)3]2 (2), [bmim]2[PdCl4] (3), and [bmpy]2[PdCl4] (4) (bmim=1‐butyl‐3‐methylimidazolium cation, bmpy=1‐butyl‐4‐methylpyridinium cation), were found to be active catalysts for the methoxycarbonylation of iodobenzene in ionic liquid (IL) media. The best results were obtained in pyridinium salts, [bmpy]X (X=Cl, Br, BF4, PF6) (76–100 % yield). In methoxycarbonylation reactions carried out in imidazolium salts, [bmim]BF4 and [bmim]PF6, the yield of benzoic acid methyl ester was slightly lower (50–78 % yield), whereas in [bmim]X (X=Cl, Br) the reaction was totally retarded. The inhibiting effect was not observed when a Me group was present at C‐2 (instead of a proton) on the imidazole ring. A palladium‐carbene complex, Pd(bmimy)2Br2 (5), obtained in the reaction of a palladium catalyst precursor with [bmim]Cl, presented much lower activity than precursors 1–4. Its formation may explain the observed inhibition of methoxycarbonylation in a [bmim]Cl medium.
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