Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine
作者:Sergei F. Vasilevsky、Maria P. Davydova、Victor I. Mamatyuk、Nikolay Tsvetkov、Audrey Hughes、Denis S. Baranov、Igor V. Alabugin
DOI:10.1071/ch17026
日期:——
Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡Cbond 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
1,2-二氨基乙烷(乙二胺)与缺电子的炔烃反应会导致C≡C键完全断裂,即使没有直接连接到炔烃上的酮基也是如此。该方法涉及将炔烃碳之一氧化成2 - R -4,5-二氢咪唑的C2,同时将另一个碳还原成甲基。这项工作中所述的Sonogashira与乙二胺介导的片段化偶联的序列可用于甲基或4,5-二氢咪唑-2-基部分选择性取代芳基卤化物中的卤素。