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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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 › peer-review

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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.",

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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.

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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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