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Updated: Jan 19, 2026

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Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification.

Brian J Groendyke1, Atanu Modak1, Silas P Cook1

  • 1Department of Chemistry , Indiana University , 800 East Kirkwood Avenue , Bloomington , Indiana 47405-7102 , United States.

The Journal of Organic Chemistry
|September 17, 2019
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Summary

Substoichiometric iron enables selective thioetherification of unactivated C-H bonds using silylperoxides. This iron-catalyzed reaction offers a novel method for functionalizing remote C-H sites with broad scope and tolerance.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-hydrogen (C-H) bond functionalization is a cornerstone of synthetic chemistry.
  • Developing methods for selective functionalization of unactivated aliphatic C-H bonds remains a significant challenge.
  • Iron catalysis offers a cost-effective and sustainable alternative to precious metal catalysts.

Purpose of the Study:

  • To develop a novel iron-catalyzed method for the thioetherification of unactivated aliphatic C-H bonds.
  • To explore the use of silylperoxides as directing groups and oxidants in C-H functionalization.
  • To investigate the scope and limitations of the developed catalytic system.

Main Methods:

  • Utilized substoichiometric amounts of iron(II) triflate as the catalyst.
  • Employed TIPS-protected peroxides with primary, secondary, and tertiary C-H sites.
  • Reacted substrates with diaryl disulfides to achieve thioetherification.
  • Conducted mechanistic studies including radical trapping experiments.

Main Results:

  • Achieved chemoselective thioetherification of remote C-H bonds.
  • Demonstrated broad substrate scope and excellent functional group tolerance.
  • The reaction proceeded efficiently without the need for noble metal additives.
  • Mechanistic investigations indicated a 1,5-H atom abstraction pathway involving a hydroxyl radical generated by iron.

Conclusions:

  • Established a novel and efficient iron-catalyzed thioetherification of unactivated C-H bonds.
  • The method provides a valuable tool for the late-stage functionalization of complex molecules.
  • Highlights the potential of iron catalysis in C-H activation and functionalization strategies.