: 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.

Rapisarda L., Fermi A., Ceroni P., Giovanelli R., Bertuzzi G., Bandini M. (2023). Electrochemical C(sp3)-H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction. CHEMICAL COMMUNICATIONS, 59(18), 2664-2667 [10.1039/d2cc06999g].

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

Rapisarda L.;Fermi A.;Ceroni P.;Giovanelli R.;Bertuzzi G.;Bandini M.
2023

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.
2023
Rapisarda L., Fermi A., Ceroni P., Giovanelli R., Bertuzzi G., Bandini M. (2023). Electrochemical C(sp3)-H functionalization of ethers via hydrogen-atom transfer by means of cathodic reduction. CHEMICAL COMMUNICATIONS, 59(18), 2664-2667 [10.1039/d2cc06999g].
Rapisarda L.; Fermi A.; Ceroni P.; Giovanelli R.; Bertuzzi G.; Bandini M.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/925515
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