Kaiser oxime resin-derived palladacycle: A recoverable polymeric precatalyst in Suzuki–Miyaura reactions in aqueous media

Abstract

Abstract Representative cross-coupling reactions of aryl bromides with different types of aryl-, alkyl, trivinylboroxine–pyridine complex, and alkenylboronic acids are performed using a polymer-bonded palladacycle derived from Kaiser oxime resin as precatalyst and potassium carbonate as base under water reflux. These processes afford biphenyls, alkylbenzenes, styrenes, and stilbenes, respectively. The same boronic acids can be cross-coupled with representative allyl and benzyl chlorides using KOH as base in aqueous acetone at 50 °C providing allylbenzenes, diarylmethanes, and 1,4-pentadienes. The palladated polymer can be recovered by filtration and reused during 3–9 cycles with up to 5% of Pd leaching in each run. Very low Pd leaching levels in the crude product can be determined by ICP–OES analyses. The reaction does not work when Hg(0) is added. TEM analyses from the solution indicate the formation of Pd nanoparticles.