Abstract
Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
| Original language | English |
|---|---|
| Pages (from-to) | 421-429 |
| Number of pages | 9 |
| Journal | Australian Journal of Chemistry |
| Volume | 70 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1 Jan 2017 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
Cite this
Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine. / Vasilevsky, Sergei F.; Davydova, Maria P.; Mamatyuk, Victor I.; Tsvetkov, Nikolay; Hughes, Audrey; Baranov, Denis S.; Alabugin, Igor V.
In: Australian Journal of Chemistry, Vol. 70, No. 4, 01.01.2017, p. 421-429.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine
AU - Vasilevsky, Sergei F.
AU - Davydova, Maria P.
AU - Mamatyuk, Victor I.
AU - Tsvetkov, Nikolay
AU - Hughes, Audrey
AU - Baranov, Denis S.
AU - Alabugin, Igor V.
PY - 2017/1/1
Y1 - 2017/1/1
N2 - Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
AB - Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
UR - http://www.scopus.com/inward/record.url?scp=85016809022&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85016809022&partnerID=8YFLogxK
U2 - 10.1071/CH17026
DO - 10.1071/CH17026
M3 - Article
VL - 70
SP - 421
EP - 429
JO - Australian Journal of Chemistry
JF - Australian Journal of Chemistry
SN - 0004-9425
IS - 4
ER -