Electrochemical Organoselenium Catalysis for the Selective Activation of Alkynes: Easy Access to Carbonyl-pyrroles/oxazoles from N-Propargyl Enamines/Amides.

Abstract

Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes was attained to access carbonyl-pyrroles or -oxazoles from N-propargyl derivatives. Organoselenium was employed as the electrocatalyst, which played a crucial role as a π-Lewis acid and selectively activated the alkyne for the successful nucleophilic addition. The synthetic strategy permits a wide range of substrate scope up to 93% yield. Several mechanistic experiments, including the isolation of a selenium-incorporated intermediate adduct, enlighten the electrocatalytic pathway.