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Electrolysis03:00

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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Voltammetric Techniques: Cyclic Voltammetry01:10

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Cyclic voltammetry (CV) is an electrochemical technique used to investigate the redox properties of a chemical species. It involves measuring the current response of an electrochemical cell as a function of the applied potential. The setup for cyclic voltammetry typically consists of a working electrode, a reference electrode, and a counter electrode—all immersed in an electrolyte solution. The working electrode is where the redox reaction of interest occurs, while the reference electrode...
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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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Interfacial Electrochemical Methods: Overview01:06

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Interfacial electrochemical methods focus on the phenomena occurring at the boundary between an electrode and a solution, as opposed to bulk methods that concentrate on the solution's overall properties. These interfacial methods are classified as either static or dynamic based on the presence of a nonzero current in the electrochemical cell and the consistency of analyte concentrations. Static methods, such as potentiometry, measure the cell's potential without any significant current...
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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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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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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Continuous Flow Electrochemistry Enables Practical and Site-Selective C-H Oxidation.

Tian-Sheng Chen1, Hao Long1, Yuxing Gao1

  • 1State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.

Angewandte Chemie (International Ed. in English)
|August 17, 2023
PubMed
Summary

This study introduces a novel electrochemical method for selectively oxidizing benzylic C(sp3)-H bonds to alcohols. This cost-efficient approach in continuous flow reactors avoids catalysts and offers high selectivity and scalability for organic synthesis.

Keywords:
AlcoholContinuous FlowC−H FunctionalizationElectrochemistryOxidation

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Sustainable Chemistry

Background:

  • Selective C(sp3)-H bond oxygenation is crucial for synthesizing functionalized molecules.
  • Oxidizing C(sp3)-H bonds to alcohols is challenging due to similar bond strengths and product over-oxidation.
  • Existing methods often lack selectivity or require harsh conditions.

Purpose of the Study:

  • To develop a practical, cost-efficient, and highly selective electrochemical method for benzylic C(sp3)-H bond monooxygenation.
  • To demonstrate the method's broad scope, scalability, and unique mechanism.
  • To provide an alternative to traditional oxidation methods, avoiding catalysts and chemical oxidants.

Main Methods:

  • Utilizing continuous flow reactors for electrochemical oxidation of benzylic C(sp3)-H bonds.
  • Employing a sequential electron/proton transfer mechanism for selective C-H bond cleavage.
  • Producing trifluoroacetate esters, which are hydrolyzed to target benzylic alcohols.

Main Results:

  • Achieved highly selective monooxygenation of benzylic C(sp3)-H bonds.
  • Demonstrated a broad substrate scope and exceptional site selectivity.
  • Showcased excellent scalability with production of 115 g of an alcohol product.
  • Confirmed the mechanism involves sequential electron/proton transfer, distinct from hydrogen atom transfer (HAT).

Conclusions:

  • The developed electrochemical method offers a practical, scalable, and highly selective route for benzylic alcohol synthesis.
  • The method's unique mechanism provides superior control over C-H bond oxygenation compared to traditional approaches.
  • This catalytic-free, oxidant-free electrochemistry presents a greener alternative for industrial applications in organic synthesis.