Oxadiazoline and ketoimine palladium(II) complexes supported on a chitosan membrane and their catalytic activity for the microwave-assisted Suzuki Miyaura cross-coupling in water

The fused bicyclic Delta 4-1,2,4-oxadiazoline trans-( PdCl2 {N=C(R)ONC(H)CH2CH2CMe2}(2)]) palladium(II) complex 1 (R=p-ClC6H4), in refluxing chloroform, undergoes N-O bond cleavage of the oxadiazoline ring to furnish the new ketoimine palladium(II) complex trans-([PdCl2{N(C(=O)(R))=6CH(2)CH(2)C(Me-2)NH}(2)]) 2 bearing the 4-chloro-N-(5,5-dimethylpyrrolidin-2-ylidene)benzamide ligands. Complexes 1 (R = Me) and 2 (R=p-ClC6H4) 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. (C) 2011 Elsevier B.V. All rights reserved.