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 language | English |
|---|---|
| Pages (from-to) | 5512-5515 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 52 |
| Issue number | 42 |
| DOIs | |
| State | Published - Oct 19 2011 |
Fingerprint
All Science Journal Classification (ASJC) codes
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Fast dye salts provide fast access to azidoarene synthons in multi-step one-pot tandem click transformations. / Fletcher, James T.; Reilly, Jacqueline E.
In: Tetrahedron Letters, Vol. 52, No. 42, 19.10.2011, p. 5512-5515.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=80052793388&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80052793388&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2011.08.069
DO - 10.1016/j.tetlet.2011.08.069
M3 - Article
VL - 52
SP - 5512
EP - 5515
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 42
ER -