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Related Concept Videos

Anoxygenic Photosynthesis01:30

Anoxygenic Photosynthesis

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Anoxygenic photosynthesis is a phototrophic process that captures light energy to drive carbon fixation without producing molecular oxygen. Unlike oxygenic photosynthesis, which utilizes water as an electron donor and releases oxygen, anoxygenic phototrophs use alternative electron donors such as hydrogen sulfide (H₂S), elemental sulfur (S⁰), or thiosulfate (S₂O₃²⁻). This process is carried out by diverse groups of bacteria, including purple bacteria, green...
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The Z-Scheme of Electron Transport in Photosynthesis01:34

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The light reactions of photosynthesis assume a linear flow of electrons from water to NADP+. During this process, light energy drives the splitting of water molecules to produce oxygen. However, oxidation of water molecules is a thermodynamically unfavorable reaction and requires a strong oxidizing agent. This is accomplished by the first product of light reactions: oxidized P680 (or P680+), the most powerful oxidizing agent known in biology. The oxidized P680 that acquires an electron from the...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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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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Voltaic/Galvanic Cells02:47

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Spontaneous Chemical Reactions
Spontaneous redox reactions occur abundantly in nature. The chemical reaction occurring in a disposable AA battery powering our remote controls is one such example of a spontaneous redox reaction. Another example is the immersion of coiled copper wire into an aqueous silver nitrate solution. The reaction shows a gradual, visually impressive color change from colorless to bright blue and the formation of a grey precipitate on the copper wire. In this experiment,...
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Quinone-mediated hydrogen anode for non-aqueous reductive electrosynthesis.

Jack Twilton1, Mathew R Johnson1, Vinayak Sidana1

  • 1Department of Chemistry, University of Wisconsin-Madison, Madison, WI, USA.

Nature
|August 21, 2023
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Summary

A novel mediated hydrogen (H2) anode enables sustainable electrosynthetic reductions by electrochemically oxidizing H2 indirectly. This technology supports nickel-catalyzed cross-electrophile coupling reactions, advancing greener chemical synthesis.

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Area of Science:

  • Green Chemistry
  • Electrochemistry
  • Organic Synthesis

Background:

  • Electrochemical synthesis offers sustainable routes to industrial chemicals.
  • Electrosynthetic reductions typically require external electron sources, often relying on sacrificial anodes.
  • Anodic water oxidation is appealing but limited by anhydrous reaction condition requirements, highlighting the need for alternative reductant sources like H2.

Purpose of the Study:

  • To develop a sustainable, mediated hydrogen anode for electrosynthetic reductions under non-aqueous conditions.
  • To enable indirect electrochemical oxidation of H2 using a quinone mediator.
  • To apply this technology to challenging reactions like nickel-catalyzed cross-electrophile coupling (XEC).

Main Methods:

  • A mediated H2 anode was developed by coupling thermal catalytic hydrogenation of an anthraquinone mediator with electrochemical oxidation of the anthrahydroquinone.
  • The mediated anode was utilized to support nickel-catalyzed cross-electrophile coupling (XEC) reactions.
  • The method was validated in small-scale batch reactions and scaled up in a recirculating flow reactor.

Main Results:

  • The quinone-mediated H2 anode successfully supported nickel-catalyzed XEC reactions.
  • Hectogram-scale synthesis of a pharmaceutical intermediate was achieved using a recirculating flow reactor.
  • The developed technology provides a general strategy for H2-driven electrosynthetic reductions.

Conclusions:

  • Mediated H2 anode technology offers a sustainable alternative to sacrificial anodes for electrosynthetic reductions.
  • This approach facilitates greener chemical manufacturing, particularly in the pharmaceutical industry.
  • The system is adaptable for both small-scale validation and large-scale synthesis.