Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction

Benedikt Dahms, Philipp J. Kohlpaintner, Anton Wiebe, Rolf Breinbauer, Dieter Schollmeyer, Siegfried R. Waldvogel

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4′-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4′-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

Original languageEnglish
Pages (from-to)2713-2716
Number of pages4
JournalChemistry - A European Journal
Volume25
Issue number11
DOIs
Publication statusPublished - 21 Feb 2019

Fingerprint

Phenols
Electricity
Chemical activation
Economics
Catalysts
Substrates
Metals

Keywords

  • anode
  • cross-coupling
  • C−H activation
  • dehydrogenation
  • electrochemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fields of Expertise

  • Human- & Biotechnology

Cite this

Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction. / Dahms, Benedikt; Kohlpaintner, Philipp J.; Wiebe, Anton; Breinbauer, Rolf; Schollmeyer, Dieter; Waldvogel, Siegfried R.

In: Chemistry - A European Journal, Vol. 25, No. 11, 21.02.2019, p. 2713-2716.

Research output: Contribution to journalArticleResearchpeer-review

Dahms, Benedikt ; Kohlpaintner, Philipp J. ; Wiebe, Anton ; Breinbauer, Rolf ; Schollmeyer, Dieter ; Waldvogel, Siegfried R. / Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction. In: Chemistry - A European Journal. 2019 ; Vol. 25, No. 11. pp. 2713-2716.
@article{c5016cb7ad124ae1a7c3be0786673bef,
title = "Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction",
abstract = "A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4′-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4′-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.",
keywords = "anode, cross-coupling, C−H activation, dehydrogenation, electrochemistry",
author = "Benedikt Dahms and Kohlpaintner, {Philipp J.} and Anton Wiebe and Rolf Breinbauer and Dieter Schollmeyer and Waldvogel, {Siegfried R.}",
note = "{\circledC} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",
year = "2019",
month = "2",
day = "21",
doi = "10.1002/chem.201805737",
language = "English",
volume = "25",
pages = "2713--2716",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH",
number = "11",

}

TY - JOUR

T1 - Selective Formation of 4,4′-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction

AU - Dahms, Benedikt

AU - Kohlpaintner, Philipp J.

AU - Wiebe, Anton

AU - Breinbauer, Rolf

AU - Schollmeyer, Dieter

AU - Waldvogel, Siegfried R.

N1 - © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

PY - 2019/2/21

Y1 - 2019/2/21

N2 - A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4′-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4′-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

AB - A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4′-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4′-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

KW - anode

KW - cross-coupling

KW - C−H activation

KW - dehydrogenation

KW - electrochemistry

UR - http://www.scopus.com/inward/record.url?scp=85060750973&partnerID=8YFLogxK

U2 - 10.1002/chem.201805737

DO - 10.1002/chem.201805737

M3 - Article

VL - 25

SP - 2713

EP - 2716

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 11

ER -