Sterically Congested 2,6-Disubstituted Anilines from Direct C?N Bond Formation at an Iodine(III) Center
2,6-Disubstituted anilines are readily prepared from the direct reaction between amides and diaryliodonium salts. As demonstrated for 24 different examples, the reaction is of unusually broad scope with respect to the sterically congested arene and the nitrogen source, occurs without the requirement for any additional promoter, and proceeds through a direct reductive elimination at the iodine(III) center. The efficiency of the coupling procedure is further demonstrated within the short synthesis of a chemerin binding inhibitor.
Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion
The copper-catalyzed N-arylation of amides, the Goldberg reaction, usually requires drastic reaction conditions and produces only moderate yields of the desired products.Much better results can be achieved by modifying the reaction conditions.We used copper on silica as a catalyst and potassium acetate as a base and continuously removed the resulting acetic acid from the reaction mixture.In this way we gained high, in some cases nearly quantitative yields of the arylated or heteroarylated products.
Renger, Bernd
p. 856 - 860
(2007/10/02)
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