Exhaustive Hydrodechlorination of Trichloroacetamides under Electrochemical Conditions at Ambient Temperature

Hydrogenation of trichloroacetamides to afford structurally diverse acetamide derivatives is achieved under environmentally benign, mild electrochemical conditions through an iodide-mediated crucial halogen-bonding interaction. The reaction mechanism is fully established by control experiments and by in situ cyclic voltammetry.

A simple yet efficient electrochemical method is developed for accessing acetamide derivatives from allylic trichloroacetamides derived from the Overman reaction, even though the transformation is synthetically challenging under reductive conditions. The proposed mechanistic pathway of the reaction is fully supported by control experiments and electrochemical studies. Other attractive features, such as inexpensive electrode material and electrolytes, minimal chemical waste, broad substrate scope, consistent yield, operational simplicity, and scalability, make this method appealing.