Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine

Sergei F. Vasilevsky, Maria P. Davydova, Victor I. Mamatyuk, Nikolay Tsvetkov, Audrey Hughes, Denis S. Baranov, Igor V. Alabugin

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)421-429
Number of pages9
JournalAustralian Journal of Chemistry
Volume70
Issue number4
DOIs
Publication statusPublished - 1 Jan 2017
Externally publishedYes

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ethylenediamine
Alkynes
Electrons
Carbon
Halogens
Substitution reactions
Oxidation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Vasilevsky, S. F., Davydova, M. P., Mamatyuk, V. I., Tsvetkov, N., Hughes, A., Baranov, D. S., & Alabugin, I. V. (2017). Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine. Australian Journal of Chemistry, 70(4), 421-429. https://doi.org/10.1071/CH17026

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 journalArticle

Vasilevsky, SF, Davydova, MP, Mamatyuk, VI, Tsvetkov, N, Hughes, A, Baranov, DS & Alabugin, IV 2017, 'Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine', Australian Journal of Chemistry, vol. 70, no. 4, pp. 421-429. https://doi.org/10.1071/CH17026
Vasilevsky, Sergei F. ; Davydova, Maria P. ; Mamatyuk, Victor I. ; Tsvetkov, Nikolay ; Hughes, Audrey ; Baranov, Denis S. ; Alabugin, Igor V. / Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine. In: Australian Journal of Chemistry. 2017 ; Vol. 70, No. 4. pp. 421-429.
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