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

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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.

Graphical abstract: Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators

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Publication details

The article was received on 14 Sep 2017, accepted on 25 Oct 2017 and first published on 06 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC04032F
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Selective electrochemical generation of benzylic radicals enabled by ferrocene-based electron-transfer mediators

    A. J. J. Lennox, J. E. Nutting and S. S. Stahl, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04032F

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