title: Pd-catalyzed Semmler-Wolff reactions for the conversion of substituted cyclohexenone oximes to primary anilines.
abstract: Homogeneous Pd catalysts have been identified for the conversion of cyclohexenone and tetralone O-pivaloyl oximes to the corresponding primary anilines and 1-aminonaphthalenes. This method is inspired by the Semmler-Wolff reaction, a classic method that exhibits limited synthetic utility owing to its forcing conditions, narrow scope, and low product yields. The oxime N-O bond undergoes oxidative addition to Pd(0)(PCy3)2, and the product of this step has been characterized by X-ray crystallography and shown to undergo dehydrogenation to afford the aniline product.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Wan Pyo
authors.initials: WP
authors.lastname: Hong
authors.forename: Andrei V
authors.initials: AV
authors.lastname: Iosub
authors.forename: Shannon S
authors.initials: SS
authors.lastname: Stahl
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000814:Aniline Compounds; D003512:Cyclohexanones; D010091:Oximes; D010165:Palladium; C023650:aniline