ortho-Benzoxylation of N-Alkyl Benzamides with Aromatic Acids Catalyzed by Ruthenium(II) Complex

A highly regioselective ortho-benzoxylation of N-alkyl benzamides with aromatic acids in the presence of [{RuCl2(p-cymene)}(2)], AgSbF6, and (NH4)(2)S2O8 in 1,2-dichloroethane at 100 degrees C for 24h affording ortho-benzoxylated N-alkyl benzamides by CH bond activation is described. Further, Ru-catalyzed alkenylation is done at the ortho CH bond of benzoxylated N-alkyl benzamides with alkenes in water solvent. Subsequently, the benzoxyl moiety of N-alkyl benzamides was converted into a hydroxyl group in the presence of base or acid. A possible reaction mechanism was proposed to account for the present coupling reaction.