Hydrogen-Bond-Promoted Metal-Free Hydroamination of Alkynes

Hydrogen-Bond-Promoted Metal-Free Hydroamination of Alkynes: J. Bahri, N. Tanbouza, T. Ollevier, M. Taillefer, F. Monnier
Synlett 2019, 30, 2086–2090

C–N bonds are ubiquitous in organic molecules and their formation is crucial in organic synthesis. Among the plethora of C–N bond-forming reactions available in the arsenal of organic chemists, the hydroamination of alkynes is a very useful process, which is generally performed under metal catalysis. Recently, Professor Thierry Ollevier from the Université Laval, Québec (Canada) and co-authors described a metal-free version of hydroamination between arylacetylenes and aliphatic secondary amines, promoted by the solvent through hydrogen bond and proton exchange.


Professor Ollevier said: “In the absence of any catalyst, additive, or even purification, (E)-enamines were synthesized by a streamlined hydroamination of alkynes in ethylene glycol as the solvent.” 

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