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TEMPO-Me: An electrochemically activated methylating agent
journal contribution
posted on 2023-05-20, 07:18 authored by Norcott, PL, Hammill, CL, Johnathon RobertsonJohnathon Robertson, Angus OldingAngus Olding, Alexander BissemberAlexander Bissember, Coote, MLBench- 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.
Funding
Collier Charitable Fund
History
Publication title
Journal of the American Chemical SocietyVolume
141Pagination
15450−15455ISSN
0002-7863Department/School
School of Natural SciencesPublisher
ACSPlace of publication
Washington, USARights statement
Copyright 2019 American Chemical SocietyRepository Status
- Restricted