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Abstract

Bench- and air-stable 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is relatively unreactive at ambient temperature in the absence of an electrochemical stimulus. In this report, we demonstrate that the one-electron electrochemical oxidation of TEMPO-Me produces a powerful electrophilic methylating agent in situ. Our computational and experimental studies are consistent with methylation proceeding via a SN2 mechanism, with a strength comparable to the trimethyloxonium cation. A protocol is developed for the electrochemical methylation of aromatic acids using TEMPO-Me.

Item Type:	Article
Authors/Creators:	Norcott, PL and Hammill, CL and Robertson, JC and Olding, A and Bissember, AC and Coote, ML
Keywords:	electrosynthesis; methylation, alkoxyamine, TEMPO
Journal or Publication Title:	Journal of the American Chemical Society
Publisher:	ACS
ISSN:	0002-7863
DOI / ID Number:	https://doi.org/10.1021/jacs.9b08634
Copyright Information:	Copyright 2019 American Chemical Society
Related URLs:	UTAS Profile: Bissember, AC
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