Abstract
Ligated Pd(ii) complexes have been studied for the catalytic oxidation of terminal olefins to their corresponding methyl ketones.
Highlights
Cationic palladium(II) complexes as catalysts for the oxidation of terminal olefins to methyl ketones using hydrogen peroxide†
Ligated Pd(II) complexes have been studied for the catalytic oxidation of terminal olefins to their corresponding methyl ketones
We discovered that if we altered the counterion from acetate and prepared the cationic analogue using weakly coordinating anions the resultant complex delivered good catalytic performance in acetonitrile; a solvent that had previously been poor for Pd(OAc)2 complexes
Summary
Cationic palladium(II) complexes as catalysts for the oxidation of terminal olefins to methyl ketones using hydrogen peroxide†. An alternative peroxide to H2O2 is tert-butyl hydroperoxide (TBHP) which has been examined for Pd(II) Wacker-type reactions since 1980.17,25 Recent work by Sigman and coworkers has demonstrated the benefits of developing ligand modulated catalysts for improving the performance of these TBHP mediated oxidations.. An alternative peroxide to H2O2 is tert-butyl hydroperoxide (TBHP) which has been examined for Pd(II) Wacker-type reactions since 1980.17,25 Recent work by Sigman and coworkers has demonstrated the benefits of developing ligand modulated catalysts for improving the performance of these TBHP mediated oxidations.26,27 Their quinoline-2-oxazoline (quinox) based catalyst is shown (Fig. 1E). We began our studies by testing Pd(OAc) with acetic acid as the solvent, as this system had previously been used by Roussel and Mimoun.18 In their studies they had focussed on aliphatic olefins and when we examined this system for styrene we found that the reaction gave a significant amount of unwanted side products. H2O2 (50 wt% in H2O). c 50 °C. d 2 mol% catalyst. e 5 mol% catalyst
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