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

Chemical Science 2018 January 15
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. Cp2 Fe0/+ ) 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.

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