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(2)O 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.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3285242 | PMC |
http://dx.doi.org/10.1016/j.tetlet.2011.08.069 | DOI Listing |
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