Silphos [PCl_{3− n}(SiO₂)_n]: A Heterogeneous Phosphine Reagent for the Regioselective Synthesis of vic-Haloalcohols

Abstract

Silphos as a silica-based phosphine [PCl_3−n (SiO₂) _n ] provides a practical method for the conversion of epoxides to vic-haloalcohols in the presence of molecular bromine, iodine, or N-halosuccinimides (NXS, X = Cl, Br, I) in CH₃CN or under solvent-free conditions at r.t. The simple filtration of heterogeneous Silphos oxide from the reaction mixture affords the pure vic-haloalcohols with excellent yields.

Keywords:

• Epoxide
• heterogeneous phosphine
• molecular halogens
• N-halosuccinimide
• Silphos
• vic-haloalcohol

Acknowledgments

The authors are grateful to the Organization of Planning and Management of Iran and Shiraz University Research Council for the support of this work.

Notes

^a Conversion was determined by GC analysis using n-octane as an internal standard.