Abstract
Arenediazonium tosylate salts have been successfully employed as a new and efficient reagent in halogenation reactions. A novel and economic protocol has been developed for the bromination and chlorination of various anilines using arenediazonium tosylate salts. A wide variety of reaction conditions were studied in acetonitrile at either room temperature or 60 °C in the presence or absence of catalyst with good to excellent yields. A surprising result showed the formation of acetanilides as a major product of aniline and methyl-substituted aniline halogenations in high yields.
| Original language | English |
|---|---|
| Pages (from-to) | 7418-7422 |
| Number of pages | 5 |
| Journal | Tetrahedron |
| Volume | 66 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 11 Sep 2010 |
Keywords
- Acetanilide
- Aniline derivatives
- Arenediazonium tosylate salt
- Halogenation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Lee, Y. M., Moon, M. E., Vajpayee, V., Filimonov, V. D., & Chi, K. W. (2010). Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts. Tetrahedron, 66(37), 7418-7422. https://doi.org/10.1016/j.tet.2010.07.005