Transition-metal-free tunable chemoselective N functionalization of indoles with ynamides.

Alexandre Hentz (1) , Pascal Retailleau (1) , Vincent Gandon (1) , Kevin Cariou (1) , Robert H Dodd (1)

1 ICSN - Institut de Chimie des Substances Naturelles

Two unprecedented N functionalizations of indoles with ynamides are described. By varying the electron-withdrawing group on the ynamide nitrogen atom, either Z-indolo-etheneamides or indolo-amidines can be selectively obtained under the same metal-free reaction conditions. The scope and synthetic potential of these reactions, as well as some mechanistic insights provided by DFT calculations, are reported.

Domaines: Chimie organique

Alexandre Hentz, Pascal Retailleau, Vincent Gandon, Kevin Cariou, Robert H Dodd. Transition-metal-free tunable chemoselective N functionalization of indoles with ynamides.. Angewandte Chemie International Edition, 2014, 53 (32), pp.8333-8337. ⟨10.1002/anie.201402767⟩. ⟨hal-01065687⟩