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ortho ‐Benzoxylation of N ‐Alkyl Benzamides with Aromatic Acids Catalyzed by Ruthenium(II) Complex
Author(s) -
Padala Kishor,
Jeganmohan Masilamani
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304646
Subject(s) - chemistry , alkyl , ruthenium , regioselectivity , medicinal chemistry , moiety , catalysis , dichloroethane , solvent , stereochemistry , organic chemistry
A highly regioselective ortho ‐benzoxylation of N ‐alkyl benzamides with aromatic acids in the presence of [{RuCl 2 ( p ‐cymene)} 2 ], AgSbF 6 , and (NH 4 ) 2 S 2 O 8 in 1,2‐dichloroethane at 100 °C for 24 h 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.