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TEMPO-Me: An electrochemically activated methylating agent


Norcott, PL and Hammill, CL and Robertson, JC and Olding, A and Bissember, AC and Coote, ML, TEMPO-Me: An electrochemically activated methylating agent, Journal of the American Chemical Society, 141 pp. 15450−15455. ISSN 0002-7863 (2019) [Refereed Article]

Copyright Statement

Copyright 2019 American Chemical Society

DOI: doi:10.1021/jacs.9b08634


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 Details

Item Type:Refereed Article
Keywords:electrosynthesis; methylation, alkoxyamine, TEMPO
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Robertson, JC (Mr Johnathon Robertson)
UTAS Author:Olding, A (Mr Angus Olding)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
ID Code:135064
Year Published:2019
Web of Science® Times Cited:30
Deposited By:Chemistry
Deposited On:2019-09-25
Last Modified:2022-08-19

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