Selective Synthesis of Sulfoxides through Oxidation of Sulfides with Sodium Hypochlorite Pentahydrate Crystals

A bienzymatic cascade for selective sulfoxidation is presented. The evolved recombinant peroxygenase from Agrocybe aegeritra catalyses the enantioselective sulfoxidation of thioanisole whereas the choline oxidase from Arthrobacter nicotianae provides the H2O2 necessary via reductive activation of ambient oxygen. The reactions are performed in choline chloride‐based deep eutectic solvents serving as co‐solvent and stoichiometric reductant at the same time. Very promising product concentrations (up to 15 mM enantiopure sulfoxide) and catalyst performances (turnover numbers of 150,000 and 2100 for the peroxygenase and oxidase, respectively) have been achieved.

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A Mild, Efficient and Highly Selective Oxidation of Sulfides to Sulfoxides Catalyzed by Lewis Acid–Urea–Hydrogen Peroxide Complex at Room Temperature

Azizi

Maleki

Hakimpoor

et al. 2017

Catal Lett

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Selective Synthesis of Sulfoxides through Oxidation of Sulfides with Sodium Hypochlorite Pentahydrate Crystals

Abstract: Oxidation of sulfides with sodium hypochlorite pentahydrate crystals (1.1 equiv) in an aqueous acetonitrile solution selectively produces the corresponding sulfoxides in high yields. This procedure is catalyst-free and environmentally benign.

Cited by 23 publications

References 5 publications

Magnesium Carbenoids in Homologation Chemistry

Magnesium Carbenoids in Homologation Chemistry

Enantioselective Sulfoxidation of Thioanisole by Cascading a Choline Oxidase and a Peroxygenase in the Presence of Natural Deep Eutectic Solvents

A Mild, Efficient and Highly Selective Oxidation of Sulfides to Sulfoxides Catalyzed by Lewis Acid–Urea–Hydrogen Peroxide Complex at Room Temperature

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