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The utilization of palladium as a catalyst plays an important role in expanding the list of organic transformations. The effectiveness of palladium as a catalyst in organic reactions is influenced by factors such as temperature, solvent, and the nature of ligands coordinating with the metal center. Notably, chiral palladium ligands are highly valuable in achieving stereoselective transformations, enabling the synthesis of enantiomerically pure compounds. This project aimed to investigate novel chiral ligands incorporating a sulfoxide group, utilizing their chiral nature derived from the sulfoxide stereocenter, for Pd(II)-catalyzed decarboxylative nitrile insertion reactions. To investigate the impact of different substituents, five analogues of 6-methyl-2,2’-bipyridine, known for its efficacy as a ligand for certain reactions, were selected for this study. The rate-determining step in the Pd(II)-catalyzed decarboxylative nitrile insertion reactions is known as the carbopalladation/nitrile insertion, prompting a comparison of the activation energies associated with this specific step across the ligands by Density Functional Theory (DFT) calculations. The results of DFT calculations demonstrated that the ligand L2, derived from 4-azaindole with a methyl group at C-5 position, was the most favorable candidate, displaying lower activation energy than its counterparts. The envisioned synthesis route for ligand L2 encompassed a six-step process, starting from the corresponding chloropyridine and involving a selective oxidation of a sulfide to the sulfoxide as the final step. Despite encountering challenges that prevented the isolation of the final product, DFT results indicate the potential of a productive ligand, offering valuable insights for future synthesis work.