TY - JOUR
T1 - Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations
AU - Fletcher, James T.
AU - Reilly, Jacqueline E.
PY - 2011/10/19
Y1 - 2011/10/19
N2 - 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.
AB - 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.
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U2 - 10.1016/j.tetlet.2011.08.069
DO - 10.1016/j.tetlet.2011.08.069
M3 - Article
AN - SCOPUS:80052793388
VL - 52
SP - 5512
EP - 5515
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 42
ER -