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.
N1 - Funding Information:
This publication was made possible by Grant No. P20 RR16469 from the National Center for Research Resources (NCRR), a component of the National Institutes of Health (NIH) and its contents are the sole responsibility of the authors and do not necessarily represent the official views of NCRR or NIH.
Copyright:
Copyright 2011 Elsevier B.V., All rights reserved.
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 -