Catalytic Antioxidant Activity of Bis-Aniline-Derived Diselenides as GPx Mimics

Herein, we describe a simple and efficient route to access aniline-derived diselenides and evaluate their antioxidant/GPx-mimetic properties. The diselenides were obtained in good yields via ipso-substitution/reduction from the readily available 2-nitroaromatic halides (Cl, Br, I). These diselenides present GPx-mimetic properties, showing better antioxidant activity than the standard GPx-mimetic compounds, ebselen and diphenyl diselenide. DFT analysis demonstrated that the electronic properties of the substituents determine the charge delocalization and the partial charge on selenium, which correlate with the catalytic performances. The amino group concurs in the stabilization of the selenolate intermediate through a hydrogen bond with the selenium.

Reaction of 2,5-dihydroxy-[1,4]-benzoquinone with nucleophiles – ipso-substitution vs. addition/elimination

ipso-Substitution vs. addition/elimination reaction depending on the type of nucleophile reacting with 2,5-dihydroxy-[1,4]-benzoquinone (DHBQ).

Aryl radical-induced desulfonylative ipso-substitution of diaryliodonium salts: an efficient route to sterically hindered biarylamines

By using vicinal aryl sulfonamide-substituted diaryliodonium salts, a cascade of desulfonylation/aryl migration was promoted by triethylamine in synthesis of sterically hindered biarylamines, which operated via a radical-induced reaction pathway.