Aromatic “Redox Tag”-assisted Diels–Alder reactions by electrocatalysis

Abstract

Electrocatalysis was employed to promote Diels-Alder reactions between electronically mismatched substrates. A catalytic amount of electricity was enough to complete the overall reactions and GC-MS monitoring and CV measurements clearly illustrated the electrocatalytic nature of the reactions, which involve an EC-backward-E mechanism. The electrocatalytic Diels-Alder reactions were rationally designed based on the concept of redox tags. The results were supported by DFT calculations.