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

Authors :
Rapisarda, Leonardo
Fermi, Andrea
Ceroni, Paola
Giovanelli, Riccardo
Bertuzzi, Giulio
Bandini, Marco
Source :
Chemical Communications; 3/4/2023, Vol. 59 Issue 18, p2664-2667, 4p
Publication Year :
2023

Abstract

The chemo- and stereoselective electrochemical allylation/alkylation of ethers is presented via a C(sp<superscript>3</superscript>)–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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
13597345
Volume :
59
Issue :
18
Database :
Complementary Index
Journal :
Chemical Communications
Publication Type :
Academic Journal
Accession number :
162130140
Full Text :
https://doi.org/10.1039/d2cc06999g