Development of Palladium Catalyzed Alkene Difunctionalization on Vinyl-Quinoline Type Substrate and Isolation of Pd-Alkyl Intermediate

The synthesis of quinoline derivatives is a continuing issue facing organic chemists in both academia and industry. To address this problem, palladium-catalyzed alkene difunctionalization was developed to be a powerful and straightforward strategy of synthetic transformations for adding diversity to organic molecules. In this thesis, Pd-catalyzed olefin difunctionalization reactions of vinyl-quinoline type substrate via generating Pd-alkyl intermediates were mainly described. The reactions described herein are pursuing three significant goals: 1) to isolate and recrystallize Pd-alkyl complexes; 2) to achieve oxidation reactions on Pd-alkyl intermediate; and 3) to investigate stereochemistry of nucleopalladation step on vinyl-quinoline starting materials