Metal-free halonium mediated acetate shifts of ynamides to access a-halo acrylamides/acrylimides

S. Kramer (1) , S.D. Friis (1) , Z. Xin (1) , Yann Odabachian (2) , T. Skrydstrup (1)

1 Department of Chemistry
2 DCSO - Laboratoire de synthèse organique

A metal-free acetate shift of 3-acetoxy ynamides to access a-iodo, bromo, and chloro acrylamides/acrylimides under very mild conditions is demonstrated. The inherent alkyne activation of ynamides is sufficient to ensure the a-halo acrylamides/acrylimides in high yields without the addition of a catalyst. In all cases high Z-stereoselectivity is observed. © 2011 American Chemical Society.

Domaines: Chimie organique

S. Kramer, S.D. Friis, Z. Xin, Yann Odabachian, T. Skrydstrup. Metal-free halonium mediated acetate shifts of ynamides to access a-halo acrylamides/acrylimides. Organic Letters, 2011, 13 (7), pp.1750-1753. ⟨10.1021/ol200269h⟩. ⟨hal-00951227⟩