1. Simple and convenient copper-catalyzed amination of aryl halides to primary arylamines using NH4OH
- Author
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Taeil Yun, Hee Seon Jung, Yungyeong Cho, and Heung Bae Jeon
- Subjects
chemistry.chemical_classification ,Base (chemistry) ,010405 organic chemistry ,Ligand ,Aryl ,Organic Chemistry ,Halide ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Solvent ,chemistry.chemical_compound ,Ammonium hydroxide ,chemistry ,Nucleophile ,Drug Discovery ,Organic chemistry ,Amination - Abstract
In this study, we investigated the direct synthesis of primary arylamines from aryl iodides and bromides by Cu-catalyzed amination using ammonium hydroxide (27% NH 3 in H 2 O) 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 NH 4 OH/DMSO, or (2) with only CuI (10 mol %) in NH 4 OH/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.
- Published
- 2016
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