Studies On The Michael Addition Reaction Catalyzed By Palladium Complexes And The Acetolysis Of Tetrahydrofuran Catalyzed By Trifluoromethanesulfonic Acid

In this thesis, the bidentate-nitrogen ligands containing oxazoline and their palladium complexes were synthesized. The palladium complexes as catalyst for Michael addition reaction and acetolysis of tetrahydrofuran catalyzed by trifluoromethanesulfonic acid at room temperature were studied. The main results obtained are as follows:1. The bidentate-nitrogen ligands containing oxazoline 1 and 2 were synthesized by the condensation of 2-cyanopyridine with amino alcohols in the present of ZnCl₂ (Scheme 1). The mechanism of the reaction was proposed. All the new compounds were characterized by IR, NMR and MS spectra.2. The compounds 1 and 2 were treated by Li₂PdCl₄ to produce the palladium complexes 4 and 5(Scheme 2). All the new compounds were characterized by IR, NMR and MS spectra. The structure of palladium complex 4 was determined by x-ray single crystal diffaction.3. The palladium complexes 4 and 5 as catalyst for Michael addition reaction of 1,3-dicarbonyl compounds withα,β-unsaturated compounds (Scheme 3) were studied. The excellent yields were obtained under optimized condition with the 2mol% loading of catalysts.4. The acetolysis of tetrahydrofuran catalyzed by trifluoromethanesulfonic acid was studied (Scheme 4). The low-cost and high-efficient method for acetolysis of tetrahydrofuran was developed. The product I (yield, 98%) and II (yield, 52%) were obtained with different conditions.