Thesis advisor: Shih-Yuan Liu / Described herein are three research projects that focused on 1) the catalytic activities of Pd/azaborine-derived biary phosphine (Senphos) complexes in 1,3-enyne difunctionalization reactions and 2) the coordination behaviors of these Pd/Senphos complexes. In the first chapter, expansion of the substrate scope and mechanistic studies of the reported Pd/Senphos catalyzed site-, regio- and trans-selective hydroboration of 1,3- enynes are described. In the second chapter, the first intermolecular site-, regio- and transselective chloroboration and cyanoboration of enynes that are enabled by the Pd/Senphos catalytic system are presented. The cyanoboration products, namely vicinal boronsubstituted alkenylnitriles, are demonstrated as versatile synthetic building blocks. In the last chapter, the κ2-P-η2-B,C coordination behavior in a series of 1,2-, 1,3- and 1,4-Senphos ligated Pd(0) or Pd(II) complexes are evaluated based on solid-state structures and variable-temperature NMR measurements. / Thesis (PhD) — Boston College, 2021. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.