Discovery of and Mechanistic Insight into a Ligand-Modulated Palladium-Catalyzed Wacker Oxidation of Styrenes Using TBHP
- 10 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (9) , 2796-2797
- https://doi.org/10.1021/ja043203m
Abstract
We describe the discovery of a new N-heterocyclic carbene-modulated Pd catalyst for the Wacker oxidation that does not require molecular oxygen but instead uses TBHP as a reagent in this oxidation. The catalyst activity and selectivity for the oxidation of styrene derivatives to methyl ketones are among the best reported. Preliminary mechanistic studies of the catalytic system were performed and show that the origin of the carbonyl oxygen is TBHP and that the hydrogens in the product all originate from the starting olefin.Keywords
This publication has 5 references indexed in Scilit:
- Elucidating the Significance of β-Hydride Elimination and the Dynamic Role of Acid/Base Chemistry in a Palladium-Catalyzed Aerobic Oxidation of AlcoholsJournal of the American Chemical Society, 2004
- Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen‐Coupled TurnoverAngewandte Chemie International Edition in English, 2004
- Palladium-catalyzed oxidation of terminal olefins to methyl ketones by hydrogen peroxideThe Journal of Organic Chemistry, 1980
- Palladium(II) tert-butyl peroxide carboxylates. New reagents for the selective oxidation of terminal olefins to methyl ketones. The role of peroxymetalation in selective oxidative processesJournal of the American Chemical Society, 1980
- adIndustrial & Engineering Chemistry, 1962