title: Palladium-catalyzed intermolecular directed C-H amidation of aromatic ketones.
abstract: Pd-catalyzed directed ortho C-H amidation of aromatic ketones with both sulfonamides and amides has been accomplished. The use of an electron-deficient Pd complex, Pd(OTf)(2), is crucial for the success of this transformation. Some key intermediates of the reaction, that is, the cyclopalladation complexes of ketones, have been characterized by X-ray crystallography. Experimental analysis of these palladacycles and also the experimental results with N-methyl sulfonamides indicate that the new reaction does not seem to proceed through a nitrene intermediate. The utility of the newly developed reaction was demonstrated for the synthesis of useful organic intermediates such as 2- and 3-alkyl indoles and 2-aminophenyl ketones.
authors.affiliation: Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China.
authors.forename: Bin
authors.initials: B
authors.lastname: Xiao
authors.forename: Tian-Jun
authors.initials: TJ
authors.lastname: Gong
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.forename: Zhao-Jing
authors.initials: ZJ
authors.lastname: Liu
authors.forename: Lei
authors.initials: L
authors.lastname: Liu
mesh_terms: D000577:Amides / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006859:Hydrogen / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D000577:Amides; D007659:Ketones; D010165:Palladium; D002244:Carbon; D006859:Hydrogen