Palladium-Catalyzed C(sp2)-H Bond Alkylation of Ketoximes by Using the Ring-Opening of Epoxides

A palladium-catalyzed ortho-directed alkylation of O-methyl ketoximes that proceeds through a regioselective ring-opening reaction of epoxides has been demonstrated. This C(sp(2))-H activation/alkylation protocol was carried out in pivalic acid/1,1,1,3,3,3-hexafluoro-2-propanol (PivOH/HFIP, 2:8) as the solvent and was applied to various O-methyl ketoximes that contain either electron-donating or electron-withdrawing groups. Moreover, different types of epoxides were used in this alkylation reaction, which proceeded smoothly to give the corresponding products in moderate to good yields.