Main group compounds can offer viable alternatives to transition metal catalysts, some of which are not optimal due to toxicity concerns, element endangerment, and non-sustainable extraction from Earth's crust. In this work, a series of dicationic 2,6-Bis(benzimidazole-2-yl) pyridine (BZIMPY) -bound phosphorus-based Lewis acids were synthesized, characterized and tested for catalytic reactivity. The BZIMPY ligand provides rigidity and tunability, the R' substituents on the phosphorus influence the electron-deficiency at the P atom, and the counter anions can influence the reactivity and stability of the dication.