Sodium sulfate–hydrogen peroxide–sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones?

New Journal of Chemistry Pub Date: 2019-03-12 DOI: 10.1039/C8NJ06038J

Abstract

The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.

Graphical abstract: Sodium sulfate–hydrogen peroxide–sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
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