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

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

Fingerprint

Diamond
Boron
Phenol
Phenols
Diamonds
Anodes
Oxidation
Electrodes
Propanol
Electrolytes
Fabrication

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Electrochemistry

Cite this

Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling. / Gleede, Barbara; Yamamoto, Takashi; Nakahara, Kenshin; Botz, Alexander; Graßl, Tobias; Neuber, Rieke; Matthée, Thorsten; Einaga, Yasuaki; Schuhmann, Wolfgang; Waldvogel, Siegfried R.

In: ChemElectroChem, Vol. 6, No. 10, 15.05.2019, p. 2771-2776.

Research output: Contribution to journalArticle

Gleede, B, Yamamoto, T, Nakahara, K, Botz, A, Graßl, T, Neuber, R, Matthée, T, Einaga, Y, Schuhmann, W & Waldvogel, SR 2019, 'Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling', ChemElectroChem, vol. 6, no. 10, pp. 2771-2776. https://doi.org/10.1002/celc.201900225
Gleede, Barbara ; Yamamoto, Takashi ; Nakahara, Kenshin ; Botz, Alexander ; Graßl, Tobias ; Neuber, Rieke ; Matthée, Thorsten ; Einaga, Yasuaki ; Schuhmann, Wolfgang ; Waldvogel, Siegfried R. / Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling. In: ChemElectroChem. 2019 ; Vol. 6, No. 10. pp. 2771-2776.
@article{336dd87bd54045eaa540af88e6017303,
title = "Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling",
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.",
keywords = "boron-doped diamond, carbon−carbon coupling, conducting material, electrochemistry, oxidation",
author = "Barbara Gleede and Takashi Yamamoto and Kenshin Nakahara and Alexander Botz and Tobias Gra{\ss}l and Rieke Neuber and Thorsten Matth{\'e}e and Yasuaki Einaga and Wolfgang Schuhmann and Waldvogel, {Siegfried R.}",
year = "2019",
month = "5",
day = "15",
doi = "10.1002/celc.201900225",
language = "English",
volume = "6",
pages = "2771--2776",
journal = "ChemElectroChem",
issn = "2196-0216",
publisher = "John Wiley and Sons Ltd",
number = "10",

}

TY - JOUR

T1 - Influence of the Nature of Boron-Doped Diamond Anodes on the Dehydrogenative Phenol-Phenol Cross-Coupling

AU - Gleede, Barbara

AU - Yamamoto, Takashi

AU - Nakahara, Kenshin

AU - Botz, Alexander

AU - Graßl, Tobias

AU - Neuber, Rieke

AU - Matthée, Thorsten

AU - Einaga, Yasuaki

AU - Schuhmann, Wolfgang

AU - Waldvogel, Siegfried R.

PY - 2019/5/15

Y1 - 2019/5/15

N2 - 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.

AB - 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.

KW - boron-doped diamond

KW - carbon−carbon coupling

KW - conducting material

KW - electrochemistry

KW - oxidation

UR - http://www.scopus.com/inward/record.url?scp=85066477188&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85066477188&partnerID=8YFLogxK

U2 - 10.1002/celc.201900225

DO - 10.1002/celc.201900225

M3 - Article

AN - SCOPUS:85066477188

VL - 6

SP - 2771

EP - 2776

JO - ChemElectroChem

JF - ChemElectroChem

SN - 2196-0216

IS - 10

ER -