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.
N1 - Funding Information:
B.G.,T.G.,R.N.,T.M.andS.R.Whighlyappreciatethesupportby BMBFEPSYLON(FKZ13XP5016C,FKZ13XP5016D).A.B.andW.S. aregratefulforfinancialsupportbytheDeutscheForschungsge-meinschaft (DFG, German Research Foundation) under Germany’s ExcellenceStrategy–EXC-2033–projectnumber390677874.
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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
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U2 - 10.1002/celc.201900225
DO - 10.1002/celc.201900225
M3 - Article
AN - SCOPUS:85066477188
SN - 2196-0216
VL - 6
SP - 2771
EP - 2776
JO - ChemElectroChem
JF - ChemElectroChem
IS - 10
ER -