Abstract
The fused bicyclic Δ 4-1,2,4-oxadiazoline trans-( ▪) palladium(II) complex 1 (R = p-ClC 6H 4), in refluxing chloroform, undergoes N–O bond cleavage of the oxadiazoline ring to furnish the new ketoimine palladium(II) complex trans-( ▪) 2 bearing the 4-chloro-N-(5,5-dimethylpyrrolidin-2-ylidene)benzamide ligands. Complexes 1 (R = Me) and 2 (R = p-ClC 6H 4) were immobilized on a chitosan membrane and the systems acted as supported-catalysts (Pd-chit 1 and Pd-chit 2, respectively) for the model microwave-assisted Suzuki–Miyaura cross-coupling reactions in water using p-bromoanisole and phenylboronic acid to give p-methoxybiphenyl in excellent yield. The effects of catalyst loading, temperature, time, the phase-transfer agent tetrabutylammonium bromide (TBAB) and base were investigated, and the supported catalyst was recovered and reused up to seven times, with a gradual loss of catalytic activity.
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