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

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    43 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 Sept 2019

    Fingerprint

    Dive into the research topics of 'TEMPO-Me: An Electrochemically Activated Methylating Agent'. Together they form a unique fingerprint.

    Cite this