Simple and convenient copper-catalyzed amination of aryl halides to primary arylamines using NH4OH

In this study, we investigated the direct synthesis of primary arylamines from aryl iodides and bromides by Cu-catalyzed amination using ammonium hydroxide (27% NH3 in H2O) as nucleophile. In this article, two protocols are described: (1) a variety of aryl halides were treated with CuI (10 mol %) and DMEDA (15 mol %) in NH4OH/DMSO, or (2) with only CuI (10 mol %) in NH4OH/PEG300. In each case, the desired primary arylamines were obtained in excellent yields. Although DMEDA and PEG have previously been employed as a ligand or solvent, respectively, the substrates were limited or additional ligands were required for successful conversion. Notably, our new protocols do not require additional inorganic bases, whereas previous methods have used a base. As such, these new protocols are one of the most simple, convenient, and efficient methods that have been reported, to date.

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