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

Intramolecular electro-oxidativeaddition of enaminesor amidesto nonactivated alkynes was attained to access carbonyl-pyrroles or-oxazoles from N-propargyl derivatives. Organoseleniumwas employed as the electrocatalyst, which played a crucial role asa pi-Lewis acid and selectively activated the alkyne for thesuccessful nucleophilic addition. The synthetic strategy permits awide range of substrate scope up to 93% yield. Several mechanisticexperiments, including the isolation of a selenium-incorporated intermediateadduct, enlighten the electrocatalytic pathway.

Automated summary

Intramolecular electro-oxidative addition of enamines or amides to nonactivated alkynes was achieved to obtain carbonyl-pyrroles or-oxazoles from N-propargyl derivatives. Organoselenium was used as the electrocatalyst, functioning as a pi-Lewis acid to selectively activate the alkyne for successful nucleophilic addition. The synthetic strategy allows for a wide range of substrate scope with up to 93% yield. Several mechanistic experiments, including the isolation of a selenium-incorporated intermediate adduct, shed light on the electrocatalytic pathway.