Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts

Young Min Lee, Mi Eun Moon, Vaishali Vajpayee, Victor D. Filimonov, Ki Whan Chi

Research output: Contribution to journalArticle

39 Citations (Scopus)

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 languageEnglish
Pages (from-to)7418-7422
Number of pages5
JournalTetrahedron
Volume66
Issue number37
DOIs
Publication statusPublished - 11 Sep 2010

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Halogenation
Amines
Acetanilides
Aniline Compounds
Salts
Economics
Chlorination
Catalysts
Temperature
aniline

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 journalArticle

Lee, Young Min ; Moon, Mi Eun ; Vajpayee, Vaishali ; Filimonov, Victor D. ; Chi, Ki Whan. / Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts. In: Tetrahedron. 2010 ; Vol. 66, No. 37. pp. 7418-7422.
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