title: On the mechanism of the palladium-catalyzed tert-butylhydroperoxide-mediated Wacker-type oxidation of alkenes using quinoline-2-oxazoline ligands.
abstract: The mechanism of the tert-butylhydroperoxide-mediated, Pd(Quinox)-catalyzed Wacker-type oxidation was investigated to evaluate the hypothesis that a selective catalyst-controlled oxidation could be achieved by rendering the palladium coordinatively saturated using a bidentate amine ligand. The unique role of the Quinox ligand framework was probed via systematic ligand modifications. The modified ligands were evaluated through quantitative Hammett analysis, which supports a "push-pull" relationship between the electronically asymmetric quinoline and oxazoline ligand modules.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors.forename: Brian W
authors.initials: BW
authors.lastname: Michel
authors.forename: Laura D
authors.initials: LD
authors.lastname: Steffens
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007700:Kinetics; D008024:Ligands; D008956:Models, Chemical; D010080:Oxazoles / Q000737:chemistry; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry; D020122:tert-Butylhydroperoxide / Q000737:chemistry*
chemical_list: D000475:Alkenes; D008024:Ligands; D010080:Oxazoles; D011804:Quinolines; D010165:Palladium; D020122:tert-Butylhydroperoxide