Acetylide Ion (C22−) as a Synthon To Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis


  • This research was supported by the Institute of Bioengineering and Nanotechnology, Biomedical Research Council, Agency for Science, Technology and Research, Singapore.


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Friendly competition: A three-component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost-efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles.