title: Catalytic oxidative 1,2-shift in 1,1'-disubstituted olefins using arene(iodo)sulfonic acid as the precatalyst and oxone as the oxidant.
abstract: An efficient, catalytic hypervalent iodine-mediated oxidative 1,2-shift of 1,1'-disubstituted olefins is described. This methodology provides concise access to homobenzylic ketones with electron-donating substituents. In the case of cyclic systems, this transformation results in ring-expanded β-benzocycloalkanones, which are useful for further elaboration.
authors.affiliation: Chemical Process Research and Development, Teva Pharmaceuticals, 383 Phoenixville Pike, Malvern, Pennsylvania 19355, United States.
authors.forename: Vikram C
authors.initials: VC
authors.lastname: Purohit
authors.forename: Shawn P
authors.initials: SP
authors.lastname: Allwein
authors.forename: Roger P
authors.initials: RP
authors.lastname: Bakale
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D016877:Oxidants / Q000737:chemistry*; D010084:Oxidation-Reduction; D013464:Sulfuric Acids / Q000737:chemistry*
chemical_list: D000475:Alkenes; D007659:Ketones; D016877:Oxidants; D013464:Sulfuric Acids; C048813:potassium peroxymonosulfuric acid