Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

Abstract

SummaryA new, efficient and mild method for the direct oxidation of selenides to selenones using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) has been developed. Noteworthy this transformation proceeds at room temperature, employs a cheap and safety oxidant and has a broad functional group tolerance. Moreover, the produced selenones could be useful intermediates for the synthesis of different heterocyclic compounds.

Green synthetic investigation and spectral characterization of some spiro pyrazolidine‐based heterocycles with potential biological activity

“…The oxidation in presence of protic solvent (ethanol) was better in yield than aprotic solvent (THF) (Scheme 2). [40][41][42][43][44][45] The chemical reactivity of the oxidizing agent (MMPP) towards chalcone derivatives 4a-h in THF due to their polarity and weak THF/water hydrogen bond. [46] Compounds 4a-h are highly reactive towards MMPP reagent.…”

“…Moreover, the green chemistry approach was employed to investigate the effect of solvent polarity in the epoxidation of chalcone derivatives 4a‐h by using magnesium monoperoxyphthalate hexahydrate (MMPP) as a versatile oxidizing agent. The oxidation in presence of protic solvent (ethanol) was better in yield than aprotic solvent (THF) (Scheme ) . The chemical reactivity of the oxidizing agent (MMPP) towards chalcone derivatives 4a‐h in THF due to their polarity and weak THF/water hydrogen bond .…”

Modern Synthetic Strategies with Organoselenium Reagents: A Focus on Vinyl Selenones

“…The first oxidation of selenides to selenoxides is fast, but the decreased electron density on the selenium atom makes selenoxides less prone to the second oxygen transfer. Even if, several strong oxidants convert selenides into selenones, i.e., KMnO 4 [6], peroxyacids or their salts [6,7], H 2 O 2 in the presence of benzenseleninic acid [8], HMPA peroxo complex of molybdenum [9], Oxone ® [10], and HOF•CH 3 CN complex [11], 3-chloroperoxybenzoic acid (m-CPBA) [12] is the reagent of choice for the oxidation of vinyl selenides (Scheme 1, route a). It is used in excess in alcoholic, ethereal or halogenated solvents.…”

Oxone‐Mediated Oxidation of Vinyl Selenides in Water

“…As a consequence, only few oxidizing agents are strong enough to convert selenides into the corresponding selenones. Organic peroxyacids, such as m ‐chloroperbenzoic acid ( m ‐CPBA) or trifluoroperacetic acid in MeOH or dichloromethane, and magnesium bis(monoperoxy phthalate) (MMPP) in alcohols or THF have been successfully employed. Hydrogen peroxide with catalytic amounts of benzenseleninic acid and inorganic oxidants such as potassium permanganate or Oxone are also suitable for the oxidation.…”