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Issue 70, 2014
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Turning unreactive copper acetylides into remarkably powerful and mild alkyne transfer reagents by oxidative umpolung

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Abstract

This is not breaking news: copper acetylides, readily available polymeric rock-stable solids, have been known for more than a century to be unreactive species and piteous nucleophiles. This lack of reactivity actually makes them ideal alkyne transfer reagents that can be easily activated under mild oxidizing conditions. When treated with molecular oxygen in the presence of simple chelating nitrogen ligands such as TMEDA, phenanthroline or imidazole derivatives, they are smoothly oxidized to highly electrophilic species that formally behave like acetylenic carbocations and can therefore be used for the mild and practical alkynylation of a wide range of nitrogen, phosphorus and carbon nucleophiles.

Graphical abstract: Turning unreactive copper acetylides into remarkably powerful and mild alkyne transfer reagents by oxidative umpolung

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Publication details

The article was received on 29 Apr 2014, accepted on 28 May 2014 and first published on 29 May 2014


Article type: Feature Article
DOI: 10.1039/C4CC03198A
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2014,50, 10008-10018
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    Turning unreactive copper acetylides into remarkably powerful and mild alkyne transfer reagents by oxidative umpolung

    G. Evano, K. Jouvin, C. Theunissen, C. Guissart, A. Laouiti, C. Tresse, J. Heimburger, Y. Bouhoute, R. Veillard, M. Lecomte, A. Nitelet, S. Schweizer, N. Blanchard, C. Alayrac and A.-C. Gaumont, Chem. Commun., 2014, 50, 10008
    DOI: 10.1039/C4CC03198A

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