Palladium and copper catalyzed one-pot Sonogashira reaction of 2-nitroiodobenzenes with aryl acetylenes and subsequent regioselective hydration in water: synthesis of 2-(2-nitrophenyl)-1-aryl ethanones

An attempted Sonogashira reaction of 2-nitroiodobenzene and phenyl acetylene catalyzed by Pd(PPh3)4/Cu in water in the presence of pyrrolidine proceeds with simultaneous regioselective hydration of the Sonogashira alkyne leading to the corresponding aryl ketone. A series of functionalized 2-(2-nitrophenyl)-1-aryl ethanones are obtained in high yields by this procedure.