Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations

James T. Fletcher, Jacqueline E. Reilly

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

This study examined whether commercially available diazonium salts could be used as efficient aromatic azide precursors in one-pot multi-step click transformations. Seven different diazonium salts, including Fast Red RC, Fast Blue B, Fast Corinth V and Variamine Blue B were surveyed under aqueous click reaction conditions of CuSO 4/Na ascorbate catalyst with 1:1 t-BuOH/H 2O solvent. Two-step tandem reactions with terminal alkyne and diyne co-reactants led to 1,2,3-triazole products in 66-88% yields, while three-step tandem reactions with trimethylsilyl-protected alkyne and diyne co-reactants led to 1,2,3-triazole products in 61-78% yields.

Original languageEnglish
Pages (from-to)5512-5515
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number42
DOIs
StatePublished - Oct 19 2011

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Triazoles
Alkynes
Coloring Agents
Salts
Azides
Catalysts
fast corinth V salt
Fast Blue B

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations. / Fletcher, James T.; Reilly, Jacqueline E.

In: Tetrahedron Letters, Vol. 52, No. 42, 19.10.2011, p. 5512-5515.

Research output: Contribution to journalArticle

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