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- W2753061809 endingPage "12503" @default.
- W2753061809 startingPage "12495" @default.
- W2753061809 abstract "Kinetic studies, isotope labeling, and in situ high-resolution mass spectrometry are used to elucidate the mechanism for the catalytic oxidation of styrenes using aqueous hydrogen peroxide (H2O2) and the cationic palladium(II) compound, [(PBO)Pd(NCMe)2][OTf]2 (PBO = 2-(pyridin-2-yl)benzoxazole). Previous studies have shown that this reaction yields acetophenones with high selectivity. We find that H2O2 binds to Pd(II) followed by styrene binding to generate a Pd-alkylperoxide that liberates acetophenone by at least two competitive processes, one of which involves a palladium enolate intermediate that has not been previously observed in olefin oxidation reactions. We suggest that acetophenone is formed from the palladium enolate intermediate by protonation from H2O2. We replaced hydrogen peroxide with t-butyl hydroperoxide and found that, although the palladium enolate intermediate was observed, it was not on the major product-generating pathway, indicating that the form of the oxidant plays a key role in the reaction mechanism." @default.
- W2753061809 created "2017-09-15" @default.
- W2753061809 creator A5021362318 @default.
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- W2753061809 creator A5034887249 @default.
- W2753061809 creator A5048314462 @default.
- W2753061809 creator A5061421429 @default.
- W2753061809 date "2017-08-29" @default.
- W2753061809 modified "2023-10-17" @default.
- W2753061809 title "Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes" @default.
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- W2753061809 doi "https://doi.org/10.1021/jacs.7b05413" @default.
- W2753061809 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28849921" @default.