15482-54-9Relevant articles and documents
Braun et al.
, p. 257 (1969)
Copper catalyzed arylation/C-C bond activation: An approach toward α-aryl ketones
He, Chuan,Guo, Sheng,Huang, Li,Lei, Aiwen
supporting information; scheme or table, p. 8273 - 8275 (2010/08/03)
An efficient arylation/C-C activation process was discovered. -Diketones with aryl halides (aryl iodides and aryl bromides) could undergo reaction smoothly in the presence of Cu(I) or Cu(II) salts in DMSO using K3 PO4 3H2 O without ligands. The role of H2 O was unprecedented, which assisted the C-C activation. Various -aryl ketones could be efficiently synthesized by this novel method. In situ monitoring of the formation of KOAc and experimentation relating to "a classic diagnostic technique for the participation of radical anion intermediates" revealed the preliminary mechanistic information for the reaction. This method is simple, general, and practical which complemented the classic method for the rapid construction of C-C bonds to a carbonyl moiety.
Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides
Inaba, Shin-ichi,Rieke, Reuben D.
, p. 1373 - 1381 (2007/10/02)
Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.
