- Ortho-benzoxylation of N-alkyl benzamides with aromatic acids catalyzed by ruthenium(II) complex
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A highly regioselective ortho-benzoxylation of N-alkyl benzamides with aromatic acids in the presence of [{RuCl2(p-cymene)}2], AgSbF6, and (NH4)2S2O8 in 1,2-dichloroethane at 100°C for 24 h affording ortho-benzoxylated N-alkyl benzamides by C-H bond activation is described. Further, Ru-catalyzed alkenylation is done at the ortho C-H 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. C-H bond activation: A highly regioselective ortho-benzoxylation of benzamides with substituted benzoic acids in the presence of a ruthenium catalyst is described. Further, Ru-catalyzed alkenylation is carried out at the ortho C-H bond of benzoxylated N-alkyl benzamides with alkenes in water solvent. Subsequently, the benzoxyl moiety of N-alkyl benzamides was converted into the hydroxyl group in the presence of base or acid (see scheme).
- Padala, Kishor,Jeganmohan, Masilamani
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supporting information
p. 4092 - 4097
(2014/04/17)
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