Electrochemical Synthesis of β-Arylamino Ketones from Tertiary Anilines and Silyl Enol Ethers

Abstract

A novel strategy for the green and efficient electrochemical synthesis of β-arylamino ketones has been developed through the reaction of readily available tertiary anilines with silyl enol ethers. This metal- and oxidant-free method operates under mild conditions and delivers β-arylamino ketones in high yields. The substrate scope with respect to various tertiary anilines and silyl enol ethers has been systematically investigated. Moreover, a continuous flow electrochemical reactor enabled the scalable synthesis of β-arylamino ketones, demonstrating the potential for industrial application. Mechanistic studies involving radical scavenging experiments and cyclic voltammetry suggest a reaction pathway involving anodically generated tertiary α-aminoalkyl radicals and subsequent C–C bond formation.