Electrocatalytic linear coupling of alkenes via radical anion under mild conditions

Abstract

The reductive coupling of alkenes is an efficient strategy for directly constructing C–C bonds from readily available bulk chemical feedstocks. Herein, a one-step electrocatalytic protocol is proposed for the direct linear coupling of alkenes. Under electrochemical conditions, the key intermediate, a highly unstable radical anion, is generated without the need for stoichiometric amounts of dangerous organolithium reagents. The radical anion undergoes a subsequent radical addition reaction, and the target compound is formed through proton capture and/or hydrogen atom transfer processes. This strategy supports both homo-coupling and cross-coupling reactions of alkenes and has been successfully applied to the synthesis of bioactive molecules. Electroredox catalysis provides a straightforward and efficient method for generating radical anions from alkenes, paving the way for the wide application of these highly reactive intermediates in chemical synthesis under mild conditions in the absence of metal and oxidant/reductant.