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TEMPO-Me: An Electrochemically Activated Methylating Agent

Norcott, Philip; Hammill, Chelsey; Noble, Dr Benjamin; Robertson, Johnathon C; Olding, Angus; Bissember, Alex C; Coote, Michelle

Description

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...[Show more]

CollectionsANU Research Publications
Date published: 2019-09-04
Type: Journal article
URI: http://hdl.handle.net/1885/209107
Source: Journal of the American Chemical Society
DOI: 10.1021/jacs.9b08634
Access Rights: Open Access

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