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TEMPO-Me: An Electrochemically Activated Methylating Agent.

Philip L Norcott1, Chelsey L Hammill1, Benjamin B Noble1

  • 1ARC Centre of Excellence for Electromaterials Science & Research School of Chemistry , Australian National University , Canberra , Australian Capital Territory 2601 , Australia.

Journal of the American Chemical Society
|September 5, 2019
PubMed
Summary
This summary is machine-generated.

Electrochemical oxidation of 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) generates a potent methylating agent. This in situ generated reagent enables efficient methylation of aromatic acids via an SN2 mechanism.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Synthetic Methodology

Background:

  • 1-methoxy-2,2,6,6-tetramethylpiperidine (TEMPO-Me) is stable but unreactive under ambient conditions without electrochemical stimulation.
  • Electrophilic methylation is a crucial transformation in organic synthesis, often requiring strong or hazardous reagents.
  • Developing mild and efficient methylation protocols is an ongoing challenge in synthetic chemistry.

Purpose of the Study:

  • To investigate the electrochemical oxidation of TEMPO-Me.
  • To demonstrate the utility of electrochemically generated TEMPO-Me as a methylating agent.
  • To develop a protocol for the methylation of aromatic acids using this system.

Main Methods:

  • One-electron electrochemical oxidation of TEMPO-Me.
  • Computational studies (e.g., DFT) to elucidate the reaction mechanism.
  • Experimental validation of methylation of aromatic acids.
  • Comparison of methylating strength with known reagents like trimethyloxonium cation.

Main Results:

  • Electrochemical oxidation of TEMPO-Me generates a potent electrophilic methylating species in situ.
  • Methylation proceeds via a SN2 mechanism, as supported by computational and experimental data.
  • The methylating strength of the generated species is comparable to trimethyloxonium cation.
  • A novel protocol for the electrochemical methylation of aromatic acids using TEMPO-Me was successfully developed.

Conclusions:

  • TEMPO-Me can be electrochemically activated to form a powerful methylating agent.
  • This method offers a new, potentially milder route for electrophilic methylation.
  • The developed protocol provides a valuable tool for the synthesis of methylated aromatic acids.