Journal
TETRAHEDRON LETTERS
Volume 52, Issue 42, Pages 5512-5515Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.08.069
Keywords
Tandem reaction; Cycloaddition; Diazonium salts; Alkynes
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Funding
- National Center for Research Resources (NCRR), a component of the National Institutes of Health (NIH) [P20 RR16469]
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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 CuSO4/Na ascorbate catalyst with 1:1 t-BuOH/H2O 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. (C) 2011 Elsevier Ltd. All rights reserved.
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