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

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

Research output: Contribution to journalArticle

149 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

ASJC Scopus subject areas

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

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    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