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 |
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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
Cite this
Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes. / Vasilevsky, Sergei F.; Krivenko, Olga L.; Gorelik, Vitalii R.; Alabugin, Igor V.
In: Tetrahedron, Vol. 64, No. 37, 08.09.2008, p. 8807-8814.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic and mechanistic aspects of cross-coupling of nitroxyl radicals of 3-imidazoline series with terminal alkynes
AU - Vasilevsky, Sergei F.
AU - Krivenko, Olga L.
AU - Gorelik, Vitalii R.
AU - Alabugin, Igor V.
PY - 2008/9/8
Y1 - 2008/9/8
N2 - 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.
AB - 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.
KW - 3-Imidazolyl-3-oxide-1-oxyls
KW - Copper salts of alkynes
KW - Cross-coupling
KW - Homocoupling
KW - Nitronylnitroxyl radicals (NNR)
KW - Terminal alkynes
KW - Transition metal catalysis
UR - http://www.scopus.com/inward/record.url?scp=48049092808&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=48049092808&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2008.06.088
DO - 10.1016/j.tet.2008.06.088
M3 - Article
AN - SCOPUS:48049092808
VL - 64
SP - 8807
EP - 8814
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 37
ER -