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 |
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Keywords
- Acetanilide
- Aniline derivatives
- Arenediazonium tosylate salt
- Halogenation
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts. / Lee, Young Min; Moon, Mi Eun; Vajpayee, Vaishali; Filimonov, Victor D.; Chi, Ki Whan.
In: Tetrahedron, Vol. 66, No. 37, 11.09.2010, p. 7418-7422.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts
AU - Lee, Young Min
AU - Moon, Mi Eun
AU - Vajpayee, Vaishali
AU - Filimonov, Victor D.
AU - Chi, Ki Whan
PY - 2010/9/11
Y1 - 2010/9/11
N2 - 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.
AB - 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.
KW - Acetanilide
KW - Aniline derivatives
KW - Arenediazonium tosylate salt
KW - Halogenation
UR - http://www.scopus.com/inward/record.url?scp=77955851381&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=77955851381&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2010.07.005
DO - 10.1016/j.tet.2010.07.005
M3 - Article
VL - 66
SP - 7418
EP - 7422
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 37
ER -