Electrochemical C(sp)-H functionalization of ethers 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 t...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2023-02, Vol.59 (18), p.2664-2667
Hauptverfasser: Rapisarda, Leonardo, Fermi, Andrea, Ceroni, Paola, Giovanelli, Riccardo, Bertuzzi, Giulio, Bandini, Marco
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Zusammenfassung: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. An electrochemical allylation/alkylation of cyclic/acyclic ethers is presented via a C(sp 3 )-H activation, proceeding under cathodic reduction. The reaction shows broad functional group tolerance and high yields.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc06999g