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Distal Ruthenaelectro-Catalyzed meta-C-H Bromination with Aqueous HBr.

Yulei Wang1, Hendrik Simon1, Xinran Chen1,2

  • 1Institut für Organische und Biomolekulare Chemie and Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität, Tammanstraße 2, 37077, Göttingen, Germany.

Angewandte Chemie (International Ed. in English)
|February 16, 2022
PubMed
Summary

Researchers developed a new electrochemical method for meta-C-H functionalization, achieving remote C-H bromination of pyrazolylarenes. This breakthrough overcomes limitations in distal C-H activation, enabling selective functionalization at the benzenoid ring.

Keywords:
C−H ActivationElectrosynthesisHalogenationsRutheniummeta-Functionalization

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Catalysis

Background:

  • Electrophilic ortho-selective C-H activation is well-established.
  • Distal C-H activation remains underdeveloped, limiting synthetic strategies.

Purpose of the Study:

  • To develop a novel electrochemical method for meta-C-H functionalization.
  • To achieve remote C-H bromination with high selectivity.

Main Methods:

  • Electrochemical bromination in an undivided cell using Ruthenium(III) chloride hydrate (RuCl3·3H2O) and aqueous hydrobromic acid (HBr).
  • Exogenous ligand- and electrolyte-free conditions were employed.
  • Mechanistic studies involving ruthenacycle formation and ligand-to-ligand hydrogen transfer (LLHT).

Main Results:

  • Successful meta-selective C-H bromination of pyrazolylarenes at the benzenoid moiety.
  • Achieved selectivity over the electron-rich pyrazole ring for the first time.
  • Demonstrated the feasibility of remote C-H functionalization via electrochemistry.

Conclusions:

  • The developed electrochemical method enables unprecedented meta-C-H functionalization.
  • The process offers a new route for selective C-H activation in complex molecules.
  • Ruthenium catalysis combined with electrochemistry provides a powerful tool for synthetic chemists.