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 |
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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 |
ASJC Scopus subject areas
- Chemistry(all)