Abstract

AbstractCarboxymethyl 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 for the 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 outcomes align with those achieved by the homogeneous counterparts, demonstrating comparable efficiency. Subsequent recycling analysis reveals a progressive decline in catalyst efficiency upon reuse, suggesting the formation of palladium black on the catalyst surface.

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