Synthesis of gem-Dihydroperoxides from Ketones and Aldehydes Using Silica Sulfuric Acid as Heterogeneous Reusable Catalyst

Abstract

Silica sulfuric acid (SSA) was found to efficiently catalyze the conversion of aldehydes and ketones directly into the corresponding gem-dihydroperoxides (DHPs) on treatment with aqueous 30% H₂O₂ at room temperature. Mild reaction conditions, good to excellent yields, short reaction times, low environmental impact, and recyclability of the catalyst are the main advantages of this synthetic method.

GRAPHICAL ABSTRACT

Keywords:

• Aldehydes
• gem-dihydroperoxides
• heterogeneous catalyst
• ketones
• silica sulfuric acid

ACKNOWLEDGMENT

We thank the research council of the University of Bu-Ali Sina for financial support to carry out this research.

Notes

^a Ketone or aldehyde (1 mmol) and 30% aqueous H₂O₂ (3 mL) in solvent (4 mL) were used at rt.

^b Reaction times for the conversion of cyclohexanone, acetophenone, and benzaldehyde, respectively.

^c Isolated yields for the conversion of cyclohexanone, acetophenone, and benzaldehyde, respectively.

^a Ketone and aldehyde (1 mmol), 30% aqueous H₂O₂ (3 mL), and CH₃CN (4 mL) were used in the presence of the catalyst (100 mg) at rt.

^b Reaction times for the conversion of cyclohexanone, acetophenone, and benzaldehyde, respectively.

^c Isolated yields for the conversion of cyclohexanone, acetophenone, and benzaldehyde, respectively.

^a Ketone and aldehyde (1 mmol), CH₃CN (4 mL), SSA (100 mg), and 30% aqueous H₂O₂ (3 mL); reactions are carried out at rt.

^b The structures of the products were established from their physical properties and spectral (¹H NMR, ¹³C NMR, and IR) analysis and compared with the data reported in the literature.

^c Isolated yield.