A convenient copper-catalyzed direct amination of nitroarenes with O-alkylhydroxylamines

✍ Scribed by Seko, Shinzo; Miyake, Kunihito; Kawamura, Norio

• Book ID: 120300165
• Publisher: Royal Society of Chemistry
• Year: 1999
• Weight: 221 KB
• Volume: 11
• Category: Article
• ISSN: 1472-7781
• DOI: 10.1039/A901537J

✦ Synopsis

O-Alkylhydroxylamines, particularly O-methylhydroxylamine, aminate nitroarenes in the presence of a strong base and a copper catalyst to give aminonitroarenes in good yields. ortho-or para-Amination with respect to the nitro group takes place, and in some cases the ortho-aminated product is preferentially obtained. With 3-substituted nitrobenzenes where the substituent has a lone pair of electrons, preferential amination occurs at the 2-position to give the sterically most congested 3c-f, 14 and 22g.