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

Autor: Lennox AJJ; Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , USA . Email: stahl@chem.wisc.edu., Nutting JE; Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , USA . Email: stahl@chem.wisc.edu., Stahl SS; Department of Chemistry , University of Wisconsin-Madison , 1101 University Avenue , Madison , Wisconsin 53706 , USA . Email: stahl@chem.wisc.edu.
Jazyk: angličtina
Zdroj: Chemical science [Chem Sci] 2017 Nov 06; Vol. 9 (2), pp. 356-361. Date of Electronic Publication: 2017 Nov 06 (Print Publication: 2018).
DOI: 10.1039/c7sc04032f
Abstrakt: 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. Cp 2 Fe 0/+ ) 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.
Databáze: MEDLINE
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