TEMPO-Me: An Electrochemically Activated Methylating Agent

Philip L. Norcott, Chelsey L. Hammill, Benjamin B. Noble, Johnathon C. Robertson, Angus Olding, Alex C. Bissember, Michelle L. Coote

Research output: Contribution to journalArticlepeer-review

29 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)15450-15455
Number of pages6
JournalJournal of The American Chemical Society
Volume141
Issue number38
DOIs
Publication statusPublished - 25 Sep 2019
Externally publishedYes

Keywords

  • methylating agents
  • TEMPO polymers
  • 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO−Me)
  • electrochemical stimulus
  • SN2 mechanism
  • electrochemical methylation

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