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Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Toward a General Protocol for Catalytic Oxidative Transformations Using Electrochemically Generated Hypervalent

Mohamed Elsherbini1, Wesley J Moran1

  • 1Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, U.K.

The Journal of Organic Chemistry
|January 23, 2023
PubMed
Summary

This study introduces a green catalytic electrosynthesis method for oxidative transformations using hypervalent iodine. This approach avoids chemical oxidants and waste, offering an efficient and scalable alternative.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Electrosynthesis

Background:

  • Hypervalent iodine reagents are effective oxidants but generate chemical waste.
  • Traditional methods often require stoichiometric oxidants and produce byproducts.

Purpose of the Study:

  • To develop a sustainable catalytic electrosynthetic protocol for oxidative transformations.
  • To utilize electricity to drive hypervalent iodine catalysis, minimizing waste.

Main Methods:

  • Catalytic electrosynthesis using an iodine(I)/iodine(III) cycle.
  • In situ generation of hypervalent iodine species.
  • Application to oxidative cyclization and α-tosyloxylation reactions.

Main Results:

  • Successful oxidative cyclization of amides and α-tosyloxylation of ketones.
  • Wide substrate scope and excellent functional group tolerance.
  • Gram-scale synthesis and catalyst recovery achieved with high efficiency.

Conclusions:

  • The developed protocol offers an environmentally friendly and efficient alternative for hypervalent iodine-mediated oxidative transformations.
  • Electrocatalysis provides a sustainable pathway for generating and utilizing hypervalent iodine species.
  • The method is robust, scalable, and applicable to diverse organic synthesis challenges.