Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions

Tobias Steinbach; Christian Wahlen; Frederik R. Wurm

doi:10.1039/c4py01365d

Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions

Tobias Steinbach, Christian Wahlen, Frederik R. Wurm^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

14 Citations (Scopus)

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Abstract

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. This journal is

Original language	English
Pages (from-to)	1192-1202
Number of pages	11
Journal	Polymer chemistry
Volume	6
Issue number	7
DOIs	https://doi.org/10.1039/c4py01365d
Publication status	Published - 21 Feb 2015
Externally published	Yes

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AB - 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. This journal is

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Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions

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