The use of a Pd(II)/Pd(0) redox couple in catalytic fluorination remains elusive, yet is desirable for selective formation of C–F bonds. We hypothesized that the ligand tri(1-adamantyl)phosphine may promote C–F reductive elimination from LPdIIAr(F) complexes by disfavoring dimerization to stabilized four-coordinate states. Density functional theory calculations suggested sterically hindered and electron deficient ligands could promote C–F reductive elimination, but synthesis of Pd–F species for experimental validation was precluded by competing decomposition under the tested conditions.