Polyvinylpyrrolidone-Supported Hydroperoxide for Selective Oxidation of Aldehydes to Carboxylic Acids and Sulfides to Sulfoxides

Abstract

The facile immobilization of hydroperoxide on the cross-linked poly(vinylpyrrolidone) is described by treatment of a poly(vinylpyrrolidone)-Vilsmeier adduct with (35%) hydrogen peroxide. The in situ–generated poly(vinyl pyrrolidone)-supported hydroperoxide reagent showed very good performance in chemoselective oxidation of aldehydes to carboxylic acids as well as sulfides to sulfoxides.

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Keywords:

• Carboxylic acid
• hydrogen peroxide
• poly(vinylpyrrolidone)
• sulfoxide
• Vilsmeier reagent

Acknowledgments

We are grateful to Mazandaran University for financial assistance of this work.

Notes

^a Reactions were performed three runs in acetonitrile at 45°C in 12 h.

^b Reactions were performed three runs in methanol at room temperature in 10 min.

^a Reactions were carried out using 0.25 g of the polymeric reagent and 2 mmol of H₂O₂.

^b Reactions were carried out using 0.5 g of the polymeric reagent and 3 mmol of H₂O₂.

^a Reaction conditions: substrate (1 mmol), PVPP-POCl₃ (0.5 g), H₂O₂ (3 mmol), MeCN (45°C).

^b Isolated yields.

^aReaction conditions: sulfide (1 mmol), PVPP-POCl₃ (0.25 g), H₂O₂ (2 mmol), MeOH, r.t.

^bIsolated yields.

^a Yield refers to the corresponding sulfone.

^b NAHBP = nicotinic acid hydrobromide perbromide.