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Cobalt‐Catalyzed C–N Bond‐Forming Reaction between Chloronitrobenzenes and Secondary Amines
Author(s) -
Toma Gabriel,
Yamaguchi Ryohei
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000862
Subject(s) - chemistry , cobalt , catalysis , organic chemistry , polymer chemistry , medicinal chemistry , combinatorial chemistry
Cyclic secondary amines react with mono‐ or dichloronitrobenzene in the presence of a catalytic amount of cobalt(II) chloride. Phosphane ligands are beneficial for the reaction, although the bite‐angle effect was not strong. The nitro‐substituted tertiary amines formed are important as bioactive compounds and can also be intermediates for the synthesis of substituted anilines. This work represents the first cobalt‐catalyzed approach to C–N bond‐forming reactions involving aromatic chlorides and cyclic secondary amines. The reaction is ortho ‐ and para ‐selective, with meta ‐substituted halides being unreactive in this procedure.