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Convenient and Practical Alkynylation of Heteronucleophiles with Copper Acetylides

Cédric Theunissen, Morgan Lecomte, Kévin Jouvin, Anouar Laouiti, Céline Guissart, Jérémy Heimburger, Estelle Loire, Gwilherm Evano*

*Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Université Libre de Bruxelles, Avenue F. D. Roosevelt 50, CP160/06, 1050 Brussels, Belgium, Email:

C. Theunissen, M. Lecomte, K. Jouvin, A. Laouiti, C. Guissart, J. Heimburger, E. Loire, G. Evano, Synthesis, 2014, 46, 1157-1166.

DOI: 10.1055/s-0033-1341025

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Stable copper acetylides can be easily activated by oxidation with oxygen in the presence of simple nitrogen ligands such as TMEDA or imidazole derivatives. Upon activation, these nucleophilic species undergo a formal umpolung and can transfer their alkyne subunit to a wide range of heteronucleophiles under especially mild conditions providing ynamides, ynimines, and alkynylphosphonates on a multigram scale.

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Key Words

copper acetylides, alkynylation, ynamides, ynimines, alkynylphosphonates

ID: J66-Y2014