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

20 Scopus citations

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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