Abstract
A new method of azide-alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
| Original language | English |
|---|---|
| Pages (from-to) | 978-985 |
| Number of pages | 8 |
| Journal | Organic Chemistry Frontiers |
| Volume | 4 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - 1 Jun 2017 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Regioselective Zn(OAc)2-catalyzed azide-alkyne cycloaddition in water : The green click-chemistry. / Morozova, Maria A.; Yusubov, Mekhman S.; Kratochvil, Bohumil; Eigner, Václav; Bondarev, Alexander A.; Yoshimura, Akira; Saito, Akio; Zhdankin, Viktor V.; Trusova, Marina E.; Postnikov, Pavel S.
In: Organic Chemistry Frontiers, Vol. 4, No. 6, 01.06.2017, p. 978-985.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Regioselective Zn(OAc)2-catalyzed azide-alkyne cycloaddition in water
T2 - The green click-chemistry
AU - Morozova, Maria A.
AU - Yusubov, Mekhman S.
AU - Kratochvil, Bohumil
AU - Eigner, Václav
AU - Bondarev, Alexander A.
AU - Yoshimura, Akira
AU - Saito, Akio
AU - Zhdankin, Viktor V.
AU - Trusova, Marina E.
AU - Postnikov, Pavel S.
PY - 2017/6/1
Y1 - 2017/6/1
N2 - A new method of azide-alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
AB - A new method of azide-alkyne cycloaddition (AAC) in the presence of Zn(OAc)2 as an inexpensive and environmentally friendly catalyst in neat water has been developed. The proposed methodology has been applied for the synthesis of 1,4-disubstituted-1,2,3-triazoles from terminal alkynes and 1,4,5-trisubstituted-1,2,3-triazoles from internal alkynes. It has been found that Zn-catalyzed AAC is extremely sensitive to steric hindrance in acetylenes and a method of regioselective triazole ring formation has been proposed. Particularly important is the isolation and characterization of a relatively stable Zn-containing intermediate, which has been characterized by NMR and HRMS.
UR - http://www.scopus.com/inward/record.url?scp=85021737763&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85021737763&partnerID=8YFLogxK
U2 - 10.1039/c6qo00787b
DO - 10.1039/c6qo00787b
M3 - Article
AN - SCOPUS:85021737763
VL - 4
SP - 978
EP - 985
JO - Organic Chemistry Frontiers
JF - Organic Chemistry Frontiers
SN - 2052-4110
IS - 6
ER -