A simple and efficient copper-catalyzed amination of aryl halides by aqueous ammonia in water

The copper(I) iodide/1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine (CuI-L2) system catalyzed the cross-coupling reactions between aryl halides and aqueous ammonia in water to produce primary aromatic amines in good yields. The protocol was simple and efficient, avoiding the need for inert atmosphere, additional base, or other additives. Key words: copper, catalysis, cross coupling, water chemistry, aqueous ammonia, primary arylamine. Le systeme iodure de cuivre(I)/1,4-bis(2-hydroxy-3,5-di-ieri-butylbenzyl)piperazine (CuI-L2) catalyse les reactions de couplages croisees entre les halogenures d'aryles et une solution aqueuse d'ammoniaque pour conduire a la formation d'amines aromatiques primaires avec de bons rendements. Le protocole est simple et efficace, il ne necessite pas d'atmosphere inerte, de base additionnelle ou d'autres additifs. Mots-cles : cuivre, catalyse, couplage croise, chimie dans l'eau, solution aqueuse d'ammoniaque, arylamine primaire.
Introduction Ammonia is an attractive source of nitrogen in organic synthesis owing to its great abundance and low cost. (1) In recent years, the palladium- or copper-catalyzed coupling of aryl [...]