This article describes an investigation of C(sp(3))O bond-forming reductive elimination reactions from Pd-IV complexes. Phenoxide, acetate, difluoroacetate, dimethylphosphate, tosylate, and nitrate nucleophiles are shown to participate in this reaction. In all cases, C(sp(3))O bond formation occurs with high selectivity over potentially competing C(sp(2))O coupling. Additives have a profound impact on the chemoselectivity of these reductive elimination reactions. An excess of RO was found to limit competing C(sp(3))C(sp(2)) bond-forming reductive elimination, while the presence of Lewis acidic cations was found to suppress competing C(sp(3))F coupling. Mechanistic investigations were conducted, and the available data are consistent with a sequence involving pre-equilibrium dissociation of the oxyanion ligand (RO ) followed by nucleophilic attack of RO on a cationic Pd(IV)alkyl intermediate.