Abstract
Coordination chemistry of a pyridine imidazole-2-ylidene ligand ( pyN ˆ C) with sterically hindered substituents toward palladium(II) metal ions has been investigated. The palladium carbene complex [( C- pyN ˆ C)Pd(η 3-allyl)Cl] ( 3) is prepared via the transmetallation from the corresponding silver carbene complexes with [ClPd(η 3-allyl)] 2. Upon the abstraction of chloride, coordination of pyridinyl-nitrogen becomes feasible to form [ C, N-( pyN ˆ C)Pd(η 3-allyl)](BF 4) ( 4). Ligand substitution reaction of 4 with triphenylphosphine results in the formation of [( C- pyN ˆ C)Pd(PPh 3)(η 3-allyl)](BF 4)], which the pyridinyl-nitrogen donor is substituted by the phosphine. This palladium complex appears to be base sensitive. Treatment of 4 with t-butoxide causes the decomposition to yield the metal nano-particles. Furthermore, de-complexation of 4 takes place under hydrogen atmosphere to generate the carbene precursor, 1-(6-mesityl-2-picolyl)-3-mesitylimidazolium salt. Nevertheless, the palladium complex 4 shows good catalytic activity on the Suzuki–Miyaura and Mizoroki–Heck reactions.
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