Electrochemical C(sp3)-H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction

The chemo- and stereoselective electrochemical allylation/alkylation of ethers is presented via a C(sp(3))-H activation event. The electrosynthetic protocol enables the realization of a large library of functionalized ethers (35 examples) in high yields (up to 84%) via cathodic activation of a new type of redox-active carbonate (RAC), capable of triggering HAT (Hydrogen-Atom-Transfer) events through the generation of electrophilic oxy radicals. The process displayed high functional group tolerance and mild reaction conditions. A mechanistic elucidation via voltammetric analysis completes the study.

Automated summary

We present the chemo- and stereoselective electrochemical allylation/alkylation of ethers via C(sp(3))-H activation. This electrosynthetic protocol allows for the synthesis of a diverse library of functionalized ethers (35 examples) in high yields (up to 84%) through cathodic activation of a new type of redox-active carbonate (RAC), which triggers HAT (Hydrogen-Atom-Transfer) events by generating electrophilic oxy radicals. The process demonstrates high functional group tolerance and mild reaction conditions. Mechanistic elucidation through voltammetric analysis completes the study.