A mechanistic and cautionary case study on the use of alternating potential in electrochemical reactions

Alfie G. Wills; Darren L. Poole; Catherine M. Alder; Marc Reid

doi:10.1002/celc.202000648

A mechanistic and cautionary case study on the use of alternating potential in electrochemical reactions

Alfie G. Wills, Darren L. Poole, Catherine M. Alder, Marc Reid

Pure And Applied Chemistry

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19 Citations (Scopus)

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Abstract

A mechanistic study on use of alternating potential (i. e. electrode polarity switching) in synthetic organic electrochemical method development using the IKA ElectraSyn 2.0 is described. Unexpected product selectivity challenges revealed that alternating potential facilitated direct, rather than mediated, electrochemical benzylic C−H oxidation of toluene derivatives. Whilst constant potential irrespective of the direction of electrode polarity was expected, our in-depth analysis revealed changes in the magnitude of applied potential with periodic switching of electrode polarity. These findings highlight an equipment engineering concern that is likely to influence and inform optimization strategies for a wide range of synthetic organic electrochemical methods under development.

Original language	English
Pages (from-to)	2771-2776
Number of pages	6
Journal	ChemElectroChem
Volume	7
Issue number	13
Early online date	2 Jun 2020
DOIs	https://doi.org/10.1002/celc.202000648
Publication status	Published - 1 Jul 2020

Keywords

electrosynthesis
oxidation
C-H activation
mechanism
degradation

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10.1002/celc.202000648Licence: CC BY 4.0

Wills-etal-CEC-2020-A-mechanistic-and-cautionary-case-study-on-the-use-of-alternating-potentialFinal published version, 4.18 MBLicence: CC BY 4.0

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation
Kerr, W. (Principal Investigator), Brown, C. (Co-investigator), Florence, A. (Co-investigator), Jamieson, C. (Co-investigator), Johnston, B. (Co-investigator), Murphy, J. (Co-investigator), Palmer, D. (Co-investigator) & Tomkinson, N. (Co-investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/01/19 → 30/09/24
Project: Research
Manganese by Numbers: A ‘Chem-Tech’ Toolbox for Innovation (Leverhulme)
Reid, M. (Fellow)
Leverhulme Trust, Glaxo Smithkline (UK)
1/01/17 → 31/12/19
Project: Research Fellowship

Cite this

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abstract = "A mechanistic study on use of alternating potential (i. e. electrode polarity switching) in synthetic organic electrochemical method development using the IKA ElectraSyn 2.0 is described. Unexpected product selectivity challenges revealed that alternating potential facilitated direct, rather than mediated, electrochemical benzylic C−H oxidation of toluene derivatives. Whilst constant potential irrespective of the direction of electrode polarity was expected, our in-depth analysis revealed changes in the magnitude of applied potential with periodic switching of electrode polarity. These findings highlight an equipment engineering concern that is likely to influence and inform optimization strategies for a wide range of synthetic organic electrochemical methods under development.",

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AU - Poole, Darren L.

AU - Alder, Catherine M.

AU - Reid, Marc

PY - 2020/7/1

Y1 - 2020/7/1

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AB - A mechanistic study on use of alternating potential (i. e. electrode polarity switching) in synthetic organic electrochemical method development using the IKA ElectraSyn 2.0 is described. Unexpected product selectivity challenges revealed that alternating potential facilitated direct, rather than mediated, electrochemical benzylic C−H oxidation of toluene derivatives. Whilst constant potential irrespective of the direction of electrode polarity was expected, our in-depth analysis revealed changes in the magnitude of applied potential with periodic switching of electrode polarity. These findings highlight an equipment engineering concern that is likely to influence and inform optimization strategies for a wide range of synthetic organic electrochemical methods under development.

KW - electrosynthesis

KW - oxidation

KW - C-H activation

KW - mechanism

KW - degradation

U2 - 10.1002/celc.202000648

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JO - ChemElectroChem

JF - ChemElectroChem

IS - 13

ER -

A mechanistic and cautionary case study on the use of alternating potential in electrochemical reactions

Abstract

Keywords

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Projects

Accelerated Discovery and Development of New Medicines: Prosperity Partnership for a Healthier Nation

Manganese by Numbers: A ‘Chem-Tech’ Toolbox for Innovation (Leverhulme)

Cite this