Enantioselective Heterogeneous Heck-Matsuda Reaction with Polymer-Supported PyOx Ligands

Carboxymethyl C5-functionalized pyridine-oxazoline(PyOx) ligands are immobilized onto Merrifield and Wang resins utilizing three distinct strategies. The immobilized PyOx ligands are employed in the Pd-catalyzed heterogeneous Heck-Matsuda reaction forthe desymmetrization of 3-cyclopenten-1-ol, resulting in the production of 20 examples of aryl-penten-1-ols with yields reaching up to 87%,and enantiomeric ratios ranging between 90:10 and 99:1. These out-comes align with those achieved by the homogeneous counterparts,demonstrating comparable efficiency. Subsequent recycling analysisreveals a progressive decline in catalyst efficiency upon reuse, suggesting the formation of palladium black on the catalyst surface.