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Electroorganic Synthesis under Flow Conditions.

Mohamed Elsherbini1, Thomas Wirth1

  • 1School of Chemistry , Cardiff University , Main Building, Park Place , Cardiff CF10 3AT , United Kingdom.

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|November 7, 2019
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Summary
This summary is machine-generated.

Flow electroorganic synthesis offers a green and scalable alternative to traditional methods. This work highlights advancements in electrochemical flow cells for efficient synthesis of valuable compounds.

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Area of Science:

  • Electroorganic synthesis
  • Green chemistry
  • Flow chemistry

Background:

  • Organic electrochemistry is experiencing a resurgence, driven by its green potential and selectivity.
  • Traditional batch electrochemistry faces limitations in scalability and electrode surface area.
  • Electrochemical flow cells offer advantages like high surface-to-volume ratios and precise control.

Purpose of the Study:

  • To showcase contributions to electroorganic synthesis using flow conditions over the past decade.
  • To present the development and application of novel electrochemical flow cells.
  • To demonstrate the efficiency and scalability of flow electrochemistry for various synthetic targets.

Main Methods:

  • Design and fabrication of multiple generations of electrochemical flow cells.
  • Application of flow cells for synthesis of diaryliodonium salts, isoindolinones, benzothiazoles, and thiazolopyridines.
  • Utilizing flow electrochemistry for continuous synthesis of hypervalent iodine reagents and subsequent transformations.
  • Integration of online analytical techniques (mass spectrometry, 2D-HPLC) for rapid optimization.

Main Results:

  • First-generation flow cell enabled synthesis of diaryliodonium salts and trifluoromethylation.
  • Second-generation flow cell facilitated gram-scale synthesis of heterocycles and hypervalent iodine reagents.
  • Commercialization of the second-generation reactor by Vapourtec Ltd.
  • Online analysis accelerated reaction optimization, including stereoselective alkoxylations.

Conclusions:

  • Electrochemical flow cells provide a powerful platform for green and scalable electroorganic synthesis.
  • Continuous flow setups overcome limitations of batch electrochemistry, enabling efficient production.
  • Online analysis significantly enhances the development and optimization of electrochemical methodologies.