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Regiospecific Synthesis of Nitroarenes by Palladium‐Catalyzed Nitrogen‐Donor‐Directed Aromatic CH Nitration
Author(s) -
Liu YunKui,
Lou ShaoJie,
Xu DanQian,
Xu ZhenYuan
Publication year - 2010
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.201002581
Subject(s) - nitration , palladium , chemistry , regioselectivity , catalysis , oxidizing agent , aryl , electrophilic aromatic substitution , organic chemistry , medicinal chemistry , nitrogen , combinatorial chemistry , alkyl
Nitration of N‐heteroaromatics : The first example of palladium‐catalyzed direct ortho ‐nitration of aryl CH bonds is described. A range of azaarenes, such as 2‐arylquinoxalines, pyridines, pyrazoles, and O ‐methyl oximes, were nitrated with excellent chemo‐ and regioselectivity (see scheme; DCE=1,2‐dichloroethane). Preliminary mechanistic investigations support a silver‐mediated radical mechanism involving palladium(II/III) and/or palladium(II/IV) catalytic cycles under oxidizing conditions.