Issue 2, 2018

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.

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

Supplementary files

Article information

Article type
Edge Article
Submitted
14 sen 2017
Accepted
25 okt 2017
First published
06 noy 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 356-361

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, 9, 356 DOI: 10.1039/C7SC04032F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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