title: Synthesis of functionalized dialkyl ketones from carboxylic acid derivatives and alkyl halides.
abstract: Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C-B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The mechanism is proposed to involve the reaction of a (L)Ni(alkyl)(2) intermediate with the carboxylic acid derivative.
authors.affiliation: Department of Chemistry, University of Rochester, Rochester, New York 14627-0216, United States.
authors.forename: Alexander C
authors.initials: AC
authors.lastname: Wotal
authors.forename: Daniel J
authors.initials: DJ
authors.lastname: Weix
mesh_terms: D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010084:Oxidation-Reduction; D011725:Pyridines / Q000737:chemistry
chemical_list: D002264:Carboxylic Acids; D004952:Esters; D006846:Hydrocarbons, Halogenated; D007659:Ketones; D011725:Pyridines; D009532:Nickel