Abstract
Mizoroki-Heck cross-coupling reaction of 4-bromoacetophenone with methyl acrylate were investigated as a model system of heterogeneous reaction in order to evaluate the performance of polyaniline supported N,N’-bis(3,5-di-tert-butylsalicylidene)propane-1,3-diaminepalladium(II) complex as catalyst. The reactions were carried out in both N,N-dimethylacetamide (DMAc) and water-DMAc mixed solvent. The performances of the catalyst in both media are comparable, giving more than 90 % conversion after 24 hours of reaction with 100 % selectivity and high isolated product yields of cinnamic esters were obtained. The used of mixed solvent gave more advantages such as less organic solvent was required and an enhanced recyclability in which the supported catalyst could be reusable at least four times without noticeable decrease in the product conversion. The properties of the catalyst was characterized by various techniques such as FTIR spectroscopy, TG-DTA, AAS, BET surface area, XRD and FESEM.
Highlights
The Heck reaction is referred to the palladium catalysed arylation or vinylation of olefins has gained prominence over past decade, as it is a selective single operational step for C-C bonds formation and has established to be an exceedingly effective and powerful tool for the carbon-carbon construction [1,2,3,4]
The numerous palladium complexes have been investigated as homogeneous catalysts and the supported palladium complexes as heterogeneous catalysts because palladium is arguably the most versatile and the most widely applied catalytic metal in Heck reaction [8,9]
Soluble phosphine palladium complex employed as catalysts for Heck reaction
Summary
The Heck reaction is referred to the palladium catalysed arylation or vinylation of olefins has gained prominence over past decade, as it is a selective single operational step for C-C bonds formation and has established to be an exceedingly effective and powerful tool for the carbon-carbon construction [1,2,3,4]. Active and well defined Schiff base metals complexes have been widely studied due to the versatility of their steric and electronic properties, which can be finetuned by choosing the amine precursors and ring substituents [13]. Due to these properties, tetradentate N2O2 ligands and their transition metal complexes often act as catalyst. In continuation of our research on the development of heterogeneous palladium catalyst for carbon-carbon bond formation, we have investigated whether a PANI supported palladium(II)-Schiff base complex could catalyzed the Mizoroki-Heck cross-coupling reaction efficiently. The catalyst can be readily recovered by simple filtration and reused for several times
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