Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling

Barbara Gleede, Takashi Yamamoto, Kenshin Nakahara, Alexander Botz, Tobias Graßl, Rieke Neuber, Thorsten Matthée, Yasuaki Einaga, Wolfgang Schuhmann, Siegfried R. Waldvogel

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Boron-doped diamond (BDD) represents a powerful and innovative electrode material. In particular, in combination with fluorinated solvents such as 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), the system exhibits the largest known electrochemical window of approximately 5 V in protic media. Furthermore, the anodic treatment allows the direct formation of oxyl radicals, which are known to exhibit specific reactivity. The electrochemical dehydrogenative phenol-phenol cross-coupling is a versatile and useful transformation to non-symmetric biphenols. This electro-organic conversion can be divided into two regimes: initial oxidation at the anode and the electrolyte-controlled follow-up reaction. This work intends to provide an answer about the influence of BDD electrodes on oxidation reactions in electrosynthesis. Depending on the electro-organic transformation, the support material of BDD, its boron content, and its fabrication method have a significant influence on the electrosynthetic efficiency.

Original languageEnglish
Pages (from-to)2771-2776
Number of pages6
JournalChemElectroChem
Volume6
Issue number10
DOIs
Publication statusPublished - 2019 May 15

Keywords

  • boron-doped diamond
  • carbon−carbon coupling
  • conducting material
  • electrochemistry
  • oxidation

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

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    Gleede, B., Yamamoto, T., Nakahara, K., Botz, A., Graßl, T., Neuber, R., Matthée, T., Einaga, Y., Schuhmann, W., & Waldvogel, S. R. (2019). Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling. ChemElectroChem, 6(10), 2771-2776. https://doi.org/10.1002/celc.201900225