Solid-Phase Organic Synthesis of 5-Iodomethyl-dihydrofuran-2-ones with Recyclable Polymer-Supported Selenium Bromide

Abstract

Reaction of polystyrene-supported selenium bromide with γ,δ-unsaturated acids and subsequent cleavage from the polymer by treatment with methyl iodide efficiently afforded 5-iodomethyl-dihydrofuran-2-ones in excellent yields. The polymeric reagent can be regenerated and reused as an environmentally friendly reagent.

GRAPHICAL ABSTRACT

Keywords:

• 5-Iodomethyl-dihydrofuran-2-one
• polystyrene-supported selenium bromide
• recyclable
• selenium-mediated intramolecular cyclization
• solid-phase organic synthesis

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 21062007), Natural Science Foundation of Jiangxi Province (No. 2008GZH0029), and the Research Program of Jiangxi Province Department of Education (No. GJJ10385).

Notes

^a Overall yields based on polymer-supported selenium bromide 1 (1.18 mmol Br/g).

^b With the third regenerated resin 1.

^c With the fourth regenerated resin 1.