896127-56-3Relevant academic research and scientific papers
Synthesis of diarylamines catalyzed by iron salts
Correa, Arkaitz,Carril, Monica,Bolm, Carsten
supporting information; experimental part, p. 10919 - 10922 (2009/11/30)
A study was conducted to demonstrate the synthesis of diarylamines catalyzed by iron salts. The study evaluated the influence acetyl as an N-protecting group. The coupling of acetanilide and iodobenzene was selected as a model reaction, to optimize the reaction conditions. It was observed that a considerable amount of the N-deprotected compound was obtained along with the desired N-acetyl diarylamine. It was also observed that diphenylamine was isolated in a significant yield, by performing a basic hydrolysis with NaOMe after the iron-catalyzed arylation. A one-pot synthesis of diphenylamine was performed by adding NaOMe to the N-arylation reaction mixture, after the acetanilide was consumed completely. It was demonstrated that the strategy overcomes the synthetic limitations associated with poor reactivity of aromatic amines under iron catalysis and serves as an alternative approach for the preparation of diarylamines.
