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Updated: Jan 19, 2026
Monitoring Equilibrium Changes in RNA Structure by 'Peroxidative' and 'Oxidative' Hydroxyl Radical Footprinting
Published on: October 17, 2011
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.
Abstract:
Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
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