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

2017 
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.
    • Correction
    • Source
    • Cite
    • Save
    • Machine Reading By IdeaReader
    26
    References
    5
    Citations
    NaN
    KQI
    []