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Redox Equilibria: Overview01:23

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A reduction-oxidation reaction is commonly called a redox reaction. In a redox reaction, electrons are transferred from one species to another rather than being shared between or among atoms. The reducing agent or reductant is the species that loses electrons and gets oxidized in the process. The species that gains electrons and gets reduced in the process is the oxidizing agent or oxidant. Redox reactions are represented as two separate equations called half-reactions, where one equation...
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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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A battery is a galvanic cell that is used as a source of electrical power for specific applications. Modern batteries exist in a multitude of forms to accommodate various applications, from tiny button batteries such as those that power wristwatches to the very large batteries used to supply backup energy to municipal power grids. Some batteries are designed for single-use applications and cannot be recharged (primary cells), while others are based on conveniently reversible cell reactions that...
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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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Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
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Electrochemical Oxidative Cross-Coupling with Hydrogen Evolution Reactions.

Yong Yuan1, Aiwen Lei1,2

  • 1College of Chemistry and Molecular Sciences, Institute for Advanced Studies (IAS) , Wuhan University , Wuhan 430072 , People's Republic of China.

Accounts of Chemical Research
|November 28, 2019
PubMed
Summary

This study showcases electrochemical oxidative cross-coupling reactions that form new chemical bonds without external oxidants, simultaneously producing hydrogen gas. These methods enable efficient synthesis of C-S, C-N, C-O, and C-P bonds, and halogenation, offering sustainable alternatives in organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Sustainable Chemistry

Background:

  • Oxidative cross-coupling is vital for forming C-C and C-heteroatom bonds.
  • Traditional methods often require stoichiometric oxidants, posing environmental concerns.
  • Developing external-oxidant-free oxidative cross-coupling aligns with sustainable chemistry principles.

Purpose of the Study:

  • To develop electrochemical oxidative cross-coupling reactions with hydrogen evolution.
  • To achieve bond formations (C-S, C-N, C-O, C-P) and halogenation under external-oxidant-free conditions.
  • To explore the application of these methods in synthesizing diverse organic molecules and heterocycles.

Main Methods:

  • Electrochemical synthesis for oxidative cross-coupling reactions.
  • Utilizing anodic oxidation to avoid external oxidants and facilitate hydrogen evolution.
  • Employing halide salts or specific organic halides as green halogenating reagents.

Main Results:

  • Successful formation of C-S bonds via cross-coupling of thiols/thiophenols with arenes, heteroarenes, and alkenes.
  • Realization of C-H amination of phenols, anilines, imidazopyridines, and ethers.
  • Development of C-H halogenation using halide salts or organic halides, and C-O bond formation.
  • Achieved C(sp2)-H and C(sp3)-H phosphonylation and S-H/S-H cross-coupling with hydrogen evolution.
  • Demonstrated alkenes difunctionalization for constructing multiple bonds (C-S/C-O, C-S/C-N, C-Se/C-O, C-Se/C-N) in one step.
  • Synthesized structurally diverse heterocyclic compounds via electrochemical oxidative annulations.

Conclusions:

  • Electrochemical oxidative cross-coupling with hydrogen evolution offers a sustainable and efficient approach for various bond formations.
  • These methods provide environmentally benign alternatives to traditional oxidative coupling reactions.
  • The developed strategies enable the synthesis of complex organic molecules and heterocycles under mild conditions.