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Controlled-Potential Coulometry: Electrolytic Methods01:17

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Controlled-potential coulometry, also known as potentiostatic coulometry, employs a three-electrode system in which the working electrode's potential is precisely regulated using a potentiostat. Platinum working electrodes are utilized for positive potentials, while mercury pool electrodes are favored for extremely negative potentials. The platinum counter electrode is separated from the analyte using a membrane or salt bridge to avoid interference in the analysis.
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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Controlled-Current Coulometry: Overview01:27

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Controlled current coulometry, also known as amperostatic coulometry, is a technique used in electrochemical analysis to measure the quantity of a substance through the controlled passage of current. It involves the application of a constant current to an electrochemical cell containing the analyte of interest. As the current flows through the cell, the analyte undergoes a redox reaction at the electrode surface, resulting in a charge transfer. By monitoring the time required for a certain...
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Electrolysis

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In a galvanic cell, the electrical work is done by a redox system on its surroundings as electrons produced by the spontaneous redox reactions are transferred through an external circuit. Alternatively, an external circuit does work on a redox system by imposing a voltage sufficient to drive an otherwise nonspontaneous reaction in a process known as electrolysis. For instance, recharging a battery involves the use of an external power source to drive the spontaneous (discharge) cell reaction in...
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Electrolyte-Controlled Regiodivergent Continuous Flow Electroselenocyclisations.

Sagar Arepally1, Hanaa Gieman1, Thomas Wirth1

  • 1School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, Cymru/Wales, CF10 3AT, UK.

Angewandte Chemie (International Ed. in English)
|August 4, 2025
PubMed
Summary
This summary is machine-generated.

Supporting electrolytes act as bases in electrochemistry, enabling selective synthesis of selenium-containing heterocycles. This continuous flow method offers a sustainable platform for creating biologically relevant compounds.

Keywords:
AlkynesContinuous flow electrochemistryElectroselenocyclisationIsoquinoline and isoindole derivativesRegioselectivity

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Area of Science:

  • Organic electrochemistry
  • Synthetic methodology
  • Heterocyclic chemistry

Background:

  • Supporting electrolytes traditionally function as ionic conductors.
  • Electrolytes can influence regioselectivity in electrochemical synthesis by acting as bases.
  • Developing selective methods for synthesizing selenium-containing heterocycles is crucial for medicinal chemistry.

Purpose of the Study:

  • To present a single-pass continuous flow electrolysis method for selective activation of diselenides and oximes.
  • To synthesize seleno-substituted isoquinoline and isoindole derivatives.
  • To explore the role of supporting electrolytes in regiodivergent electrochemical transformations.

Main Methods:

  • Single-pass continuous flow electrolysis.
  • Electrochemical activation of diselenides and oximes.
  • Mechanistic studies involving radical and ionic pathways.

Main Results:

  • Selective synthesis of seleno-substituted isoquinoline and isoindole derivatives achieved.
  • Identified radical and ionic mechanisms leading to different N-oxide products.
  • Demonstrated the utility of N-activated neutral isoquinolinium products for downstream modifications.

Conclusions:

  • Supporting electrolytes possess untapped potential in regiodivergent electrochemical synthesis.
  • The developed continuous flow method is sustainable and scalable.
  • Provides a novel platform for synthesizing biologically relevant selenium-containing heterocycles.