Switching between α-alkenylation and α-alkylation of nitriles by coupling multiple electrochemical methods

Abstract

Switching between α-alkenylation and α-alkylation of nitriles was achieved by strategically coupling multiple electrochemical redox methods. The reaction can be carried out in an undivided cell under catalyst-free and additive-free conditions. A variety of nitriles with aldehyde(hetero)arenes were selectively and efficiently converted into the corresponding α-alkenylated and α-alkylated compounds. Mechanistic studies showed that the reaction involved three processes, namely convergent paired electrolysis, sequential paired electrolysis and electroreduction. More importantly, the product distribution can be controlled by modulating the applied electrolytes.