1-Allyl- and 1-benzyl-3-methyl-1,2,3-triazolium salts via tandem click transformations

James T. Fletcher, Matthew E. Keeney, Sara E. Walz

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

A series of 1-allylated and 1-benzylated 1,2,3-triazoles with varying substituents at the 4-position were prepared in yields ranging from 74-98% using a two-step one-pot click transformation. This tandem reaction involved the nucleophilic substitution of allyl chloride and benzyl bromide with sodium azide to form organic azide intermediates followed by Cu-catalyzed Huisgen 1,3-dipolar cycloaddition with alkyne reactants in a single reaction pot without the need for sequentially separating reaction steps. 1-Allyl- and 1-benzyl-4-alkyl-1,2,3-triazoles possessing linear alkyl chains underwent efficient N-alkylation at the 3-position with methyl iodide, while tert-butyl and phenyl derivatives did not. Each of the 1-allyl- and 1-benzyl-3-methyl-4- alkyl-1,2,3-triazolium iodide salts prepared was a viscous liquid at room temperature with a stable shelf life.

Original languageEnglish
Article numberM02010SS
Pages (from-to)3339-3345
Number of pages7
JournalSynthesis
Issue number19
DOIs
StatePublished - 2010

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Triazoles
Cycloaddition
Alkylation
Substitution reactions
Salts
Sodium
Derivatives
Sodium Azide
Alkynes
Azides
Liquids
Iodides
Temperature
benzyl bromide
methyl iodide
allyl chloride

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Catalysis

Cite this

1-Allyl- and 1-benzyl-3-methyl-1,2,3-triazolium salts via tandem click transformations. / Fletcher, James T.; Keeney, Matthew E.; Walz, Sara E.

In: Synthesis, No. 19, M02010SS, 2010, p. 3339-3345.

Research output: Contribution to journalArticle

Fletcher, James T. ; Keeney, Matthew E. ; Walz, Sara E. / 1-Allyl- and 1-benzyl-3-methyl-1,2,3-triazolium salts via tandem click transformations. In: Synthesis. 2010 ; No. 19. pp. 3339-3345.
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