Efficient synthesis of 2-substituted-1,2,3-triazoles

Jarosław Kalisiak, K. Barry Sharpless, Valery V. Fokin

Research output: Contribution to journalArticle

142 Citations (Scopus)

Abstract

(Chemical Equation Presented) In this three-component reaction, alkynes undergo a copper(I)-catalyzed cycloaddition with sodium azide and formaldehyde to yield 2-hydroxymethyl-2H-1,2,3-triazoles, which are useful intermediates that can be readily converted to polyfunctional molecules. The hydroxymethyl group can also be removed, providing convenient access to NH-1,2,3-triazoles. The reaction is experimentally simple and readily scalable.

Original languageEnglish
Pages (from-to)3171-3174
Number of pages4
JournalOrganic Letters
Volume10
Issue number15
DOIs
Publication statusPublished - 2008
Externally publishedYes

Fingerprint

Triazoles
sodium azides
Sodium Azide
Alkynes
Cycloaddition
Cycloaddition Reaction
cycloaddition
alkynes
synthesis
formaldehyde
Formaldehyde
Copper
copper
Molecules
molecules

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Kalisiak, J., Sharpless, K. B., & Fokin, V. V. (2008). Efficient synthesis of 2-substituted-1,2,3-triazoles. Organic Letters, 10(15), 3171-3174. https://doi.org/10.1021/ol8006748

Efficient synthesis of 2-substituted-1,2,3-triazoles. / Kalisiak, Jarosław; Sharpless, K. Barry; Fokin, Valery V.

In: Organic Letters, Vol. 10, No. 15, 2008, p. 3171-3174.

Research output: Contribution to journalArticle

Kalisiak, J, Sharpless, KB & Fokin, VV 2008, 'Efficient synthesis of 2-substituted-1,2,3-triazoles', Organic Letters, vol. 10, no. 15, pp. 3171-3174. https://doi.org/10.1021/ol8006748
Kalisiak, Jarosław ; Sharpless, K. Barry ; Fokin, Valery V. / Efficient synthesis of 2-substituted-1,2,3-triazoles. In: Organic Letters. 2008 ; Vol. 10, No. 15. pp. 3171-3174.
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