One-pot Wittig reaction for the synthesis of α,β-unsaturated esters using highly basic magnesium/lanthanum mixed oxide

Highly basic Mg/La mixed oxide (Mg/La MO) is an effective heterogeneous base, at room temperature for the one-pot Wittig reaction involving aldehyde, α-halo esters and triphenylphosphine to afford α,β-unsaturated esters in good yields with high E-stereoselectivity. Mg/La mixed oxide was recovered quantitatively by simple filtration and reused. The basic properties of Mg/La mixed oxide have been compared to those of nanocrystalline magnesium oxide using the microcalorimetric adsorption of CO2, and the reactivity for Wittig reactions. Mg/La mixed oxide is a stronger base than magnesium oxide (MgO) but shows a much smaller number of sites. Hammett correlations have been determined for both bases and show that the reaction is base mediated, with values of ρ = 1.7 for Mg/La mixed oxide, and 1.1 for nanocrystalline magnesium oxide, and a compensation effect can then be observed.

Graphical abstractHighly basic Mg/La mixed oxide (Mg/La MO) is an effective heterogeneous base for the one-pot Wittig reaction involving aldehyde, α-halo esters and triphenylphosphine to afford α,β-unsaturated esters in good yields with high E-stereoselectivity at room temperature. The Mg/La mixed oxide was recovered quantitatively by simple filtration and reused.Figure optionsDownload full-size imageDownload high-quality image (26 K)Download as PowerPoint slide