Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates |
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Authors: | Vincent Le Fouler Guillaume Duret Philippe Bisseret Nicolas Blanchard |
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Affiliation: | Université de Haute-Alsace, Université de Strasbourg, CNRS, LIMA, UMR 7042, 68000 Mulhouse, France |
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Abstract: | Ynamides are versatile 3-atoms building blocks for organic synthesis as they participate in a variety of ionic, radical and pericyclic processes. Converting ynamides into 5-atom building blocks, such as the yet unreported N-vinyl ynamides, would open new avenues in this fascinating chemistry. We describe herein our efforts towards such goal and demonstrate that the cross-coupling between N-vinyl carbamates and bromo-alkynes using copper(I) thiophene carboxylate, 1,10-phenanthroline and tBuOK in DMSO is a reactive system with an improved profile compared to the classical ynamides syntheses. The advantages and limitations of this copper-mediated reaction are discussed. |
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Keywords: | Ynamide Copper-mediated Cross-coupling Diels-Alder |
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