Chromatography-free Wittig reactions using a bifunctional polymeric reagent

Org Lett. 2010 Nov 5;12(21):4996-9. doi: 10.1021/ol1021614.

Abstract

The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after only filtration and solvent removal.