Electrochemical C(sp3)-H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction
Leonardo Rapisarda1, Andrea Fermi1,2, Paola Ceroni1,2
1Dipartimento di Chimica "Giacomo Ciamician", Alma Mater Studiorum - Università di Bologna, via Selmi 2, 40126, Bologna, Italy. marco.bandini@unibo.it.
Abstract:
The chemo- and stereoselective electrochemical allylation/alkylation of ethers is presented via a C(sp3)-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.
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