Open Access Repository

TEMPO−Me: An electrochemically activated methylating agent

Norcott, PL, Hammill, CL, Robertson, JC, Olding, A, Bissember, AC ORCID: 0000-0001-5515-2878 and Coote, ML 2019 , 'TEMPO−Me: An electrochemically activated methylating agent' , Journal of the American Chemical Society, vol. 141 , 15450−15455 , doi: 10.1021/jacs.9b08634.

Full text not available from this repository.

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: 10.1021/jacs.9b08634
Copyright Information:

Copyright 2019 American Chemical Society

Related URLs:
Item Statistics: View statistics for this item

Actions (login required)

Item Control Page Item Control Page
TOP