A single method with a functionality switching option was developed for the first time for the Pd-catalyzed C–O cross-coupling of aryl bromides and bromo-chalcones with aldoximes. The ligand tBuXPhos (L2) was found to be an effective supporting ligand for the Pd-catalyzed coupling of aldoximes with bromo coupling partners. The functionality switching from oxime ethers to a phenolic or hydroxy group was driven by solvent or temperature. This method offers the products in good to excellent yields in short reaction times.