New Recoverable Organoselenium Catalyst for Hydroperoxide Oxidation of Organic Substrates

Abstract

New benzisoselenazol-3(2H)-one covalently bounded to a silica support was synthesized and characterized. It was used as an effective, selective, and easy-to-regenerate catalyst for t-BuOOH and H₂O₂ oxidation of alkyl arenes to alkyl aryl ketones, aromatic aldehydes to arene carboxylic acids, and sulfoxides and/or sulfones.

Keywords:

• Catalysts
• Hydrogen peroxide
• Organoselenium compounds
• Oxidation
• tert-Butyl hydroperoxide

ACKNOWLEDGMENTS

This work was supported by the Polish State Committee for Scientific Research (Grant 3T09A 003 27).

Notes

^a Data for Ebselen are given in parentheses.

^b Isolated yield based on the converted substrate.

^c TBHP used in 2.5 molar eq.

^d Accompanied by acenaphtoquinone (7ab) 21%, mp 248–251 °C (249–252 °C^{[ 23 ]}).

^e After 24 h.

^a Data for Ebselen are given in parentheses.

^b Isolated yield based on the converted substrate.

^c Reaction time 48 h.

^a Data for Ebselen are given in parentheses.

^b Reaction time for H₂O₂/HALICAT 2 h; for H₂O₂/ebselen 0.5 h.

^c Yield determined by GC, based on the converted substrate.

^d 1.2 mol of H₂O₂.

^e 2.5 mol of H₂O₂.