Development of methods to reduce energy consumption and which use non-renewable resources more efficiently is of great importance to the chemical industry. This is especially true for the production of fine chemicals and pharmaceuticals where the ratio of waste generated per quantity of product is large. Major contributions to waste stem from employing organic solvents and syntheses requiring a large number of chemical transformations. Waste can be minimized by using atom-economical reactions that promote high selectivity. Consumption of expensive transition metal catalysts is a drawback common to many catalytic reactions; therefore, development of systems that can minimize catalyst loadings and improve recyclability are of great importance. Carbon-carbon coupling reactions are an example of catalysis in need of such improvement. Suzuki-Miyaura coupling is among the most common reactions for the generation of new C-C bonds. Although well explored, the reaction still suffers from the expense of the required palladium catalyst as well as low activity in the coupling of aryl chlorides. Ionic liquids have a number of properties which make them attractive to the field of green chemistry. When used as a reaction medium, ionic liquids help prevent catalyst degradation pathways which leads to greater activity and reduction of the quantity of catalyst required. Ionic liquids can be tailored to obtain properties, such as solubility or high thermal stability, needed for a given process. Because of their unique solubility properties ionic liquids are good candidates for alleviating the high energy requirement found in solvent removal and separation of product from catalyst. This often allows for facile recycling of the expensive metal catalyst. Herein is presented research on the synthesis of an easily tunable set of ion-tagged phosphinogramine ligands for improved catalyst utility in ionic liquids. A range of steric and electronic properties was accessible by varying the substituents on phosphorus and the position of the phosphine on the indole moiety. Synthesis of metal complexes was conducted to help elucidate the electronic and steric properties of the ligands. Performance in palladium-catalyzed C-C coupling reactions was tested in ionic liquids and compared to traditional organic solvents. The results show modest catalytic activity, but are competitive with other known ionic liquid systems for difficult substrates such as aryl chlorides and electron-rich arenes. Preliminary research was also conducted on catalytic systems for asymmetric hydroformylation of styrene in ionic liquids.