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

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	https://doi.org/10.1071/CH17026
Publication status	Published - 1 Jan 2017
Externally published	Yes

ASJC Scopus subject areas

Chemistry(all)

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10.1071/CH17026

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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

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title = "Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine",

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.",

author = "Vasilevsky, {Sergei F.} and Davydova, {Maria P.} and Mamatyuk, {Victor I.} and Nikolay Tsvetkov and Audrey Hughes and Baranov, {Denis S.} and Alabugin, {Igor V.}",

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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

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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.

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