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

Alastair J.J. Lennox, Jordan E. Nutting, Shannon S. Stahl

Research output: Contribution to journalArticle (Academic Journal)peer-review

33 Citations (Scopus)
271 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)356-361
Number of pages6
JournalChemical Science
Volume9
Issue number2
Early online date6 Nov 2017
DOIs
Publication statusPublished - 1 Jan 2018

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