86896-46-0Relevant academic research and scientific papers
Development of a robust and practical process for the Darzens condensation and α,β-epoxide rearrangement: Scope and limitations of the methodology
Zimbron, Jeremy Malcolm,Seeger-Weibel, Manuela,Hirt, Hans,Gallou, Fabrice
, p. 1221 - 1226 (2008/12/22)
A practical and robust process for the Darzens condensation of substituted benzaldehydes and subsequent α,β-epoxy rearrangement is reported. The process developed is both amenable to large scale and parallel synthesis. While electron-poor benzaldehydes gave mixtures of aryl ketones and 2-substituted aryl ketones in mediocre to low yields, electron-rich benzaldehydes were found to react in high yields with complete regioselectivity to form 2-substituted aryl ketones. Georg Thieme Verlag Stuttgart.
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.
Arylation and 1-Alkenylation on α-Position of Ketones via Tributyltin Enolates Catalyzed by Palladium Complex
Kosugi, Masanori,Hagiwara, Isao,Sumiya, Takao,Migita, Toshihiko
, p. 241 - 246 (2007/10/02)
The reaction of tributyltin enolates, prepared from tributyltin methoxide and enol acetates in situ, with aryl and 1-alkenyl bromides in the presence of dichlorobis(tri-o-tolylphosphine)palladium was found to give α-aryl and α-(1-alkenyl) ketones, respectively, in good yields with essentially complete retention of the enol acetate regiochemistry.
METALLIC NICKEL: A COUPLING REAGENT OF BENZYL HALIDES AND ACYL HALIDES TO YIELD BENZYL KETONES
Inaba, Shin-ichi,Rieke, Reuben D.
, p. 2451 - 2452 (2007/10/02)
Metallic nickel was found to be a convenient reductive coupling reagent for the preparation of benzyl ketones by the reaction of benzyl halides with acyl halides.
