Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators.

ABSTRACT: The generation and intermolecular functionalisation of carbon-centred radicals has broad potential synthetic utility. Herein, we show that benzylic radicals may be generated electrochemically from benzylboronate derivatives at low electrode potentials (ca. -0.3 V vs. Cp2Fe0/+) via single electron oxidation. Use of a catalytic quantity of a ferrocene-based electron-transfer mediator is crucial to achieve successful radical functionalisation and avoid undesirable side reactions arising from direct electrochemical oxidation or from the use of stoichiometric ferrocenium-based oxidants.

SUBMITTER: Lennox AJJ 

PROVIDER: S-EPMC5909123 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature