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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: gevanoulb.ac.be

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 (free Supporting Information)


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Abstract

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