Regiospecific Synthesis of Nitroarenes by Palladium‐Catalyzed Nitrogen‐Donor‐Directed Aromatic CH Nitration | Zendy

Liu YunKui | Zendy; Lou ShaoJie | Zendy; Xu DanQian | Zendy; Xu ZhenYuan | Zendy

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Regiospecific Synthesis of Nitroarenes by Palladium‐Catalyzed Nitrogen‐Donor‐Directed Aromatic CH 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.

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