Abstract
Practical synthetic approaches to the new class of acetylenic derivatives of 3-imidazolyl-3-oxide-1-oxyls, including biradicals, were developed through cross-coupling reactions of 3-imidazolyl halides with either terminal alkynes or their copper salts. The presence of nitroxyl functional group as an internal oxidant leads to a competition between the formation of cross-coupling products and the products of oxidative homocoupling. The balance in this competition can be shifted toward the cross-coupling products through the combination of factors that includes nature of the catalyst, reactivity of the halides, and reaction conditions.
| Original language | English |
|---|---|
| Pages (from-to) | 8807-8814 |
| Number of pages | 8 |
| Journal | Tetrahedron |
| Volume | 64 |
| Issue number | 37 |
| DOIs | |
| Publication status | Published - 8 Sep 2008 |
| Externally published | Yes |
Keywords
- 3-Imidazolyl-3-oxide-1-oxyls
- Copper salts of alkynes
- Cross-coupling
- Homocoupling
- Nitronylnitroxyl radicals (NNR)
- Terminal alkynes
- Transition metal catalysis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry
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Cite this
Vasilevsky, S. F., Krivenko, O. L., Gorelik, V. R., & Alabugin, I. V. (2008). Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes. Tetrahedron, 64(37), 8807-8814. https://doi.org/10.1016/j.tet.2008.06.088