Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactionsElectronic supplementary information (ESI) available. See DOI: 10.1039/c4py01365d

A novel, general protocol for a polymer-mediated Horner-Wadsworth-Emmons (HWE) reaction is reported. The polyvalent polymeric reagent was prepared via acyclic diene metathesis (ADMET) polymerization. Homo- and copolymers of reactive poly(phosphonate)s with molecular weights up to 40 000 g·mol −1 and molecular weight dispersities < 2 were successfully synthesized. Subsequent application of these polymers in the HWE reaction to prepare a library of aromatic α,β-unsaturated ketones (chalcons) has proven to be an efficient synthetic pathway to minimize purification efforts, as the polymeric side-product can be removed by simple precipitation. In this paper we also demonstrate for the first time the preparation of a linear polyphosphate from a polyalkylphosphonate. Poly(phosphonate)s were used in Horner-Wadsworth-Emmons (HWE) reactions with aldehydes. The progress of the reaction was monitored via in situ -NMR spectroscopy. Minimal purification efforts by precipitation of the polymer are achieved.