64024-59-5Relevant academic research and scientific papers
Uncatalyzed conjugate addition of organozinc halides to enones in DME: A combined experimental/computational study on the role of the solvent and the reaction mechanism
Casotti, Gianluca,Ciancaleoni, Gianluca,Lipparini, Filippo,Nieri, Chiara,Iuliano, Anna
, p. 257 - 263 (2019/12/30)
Both aryl and alkylzinc halides prepared by direct insertion of zinc into organic halides in the presence of LiCl underwent the conjugate addition reaction to nonenolizable unsaturated ketones in excellent yield, provided that DME was used instead of THF as the solvent. Diffusion NMR measurements highlighted that the species undergo considerable aggregation under the experimental conditions used in the synthetic procedure, but no substantial differences have been found between the two solvents. Density functional theory calculations, prompted by the experimental aggregation study, revealed an unexpected reaction mechanism, where the coordinating capabilities of DME stabilize a transition state involving two organozinc moieties, lowering the activation energy of the reaction with respect to that seen for THF, enough to explain the fast and quantitative reactions observed experimentally and the different behaviors of the two solvents.
Stable and Reusable Palladium Nanoparticles-Catalyzed Conjugate Addition of Aryl Iodides to Enones: Route to Reductive Heck Products
Parveen, Naziya,Saha, Rajib,Sekar, Govindasamy
, p. 3741 - 3751 (2017/11/15)
An efficient, binaphthyl-backbone-stabilized palladium nanoparticles (Pd-BNP) catalyst for the 1,4-addition of aryl halides to enones has been developed. The scope of the reaction has been studied with various substituted and sterically hindered aryl hali
Direct functionalization of benzylic C-Hs with vinyl acetates via Fe-catalysis
Song, Chun-Xiao,Cai, Gui-Xin,Farrell, Thomas R.,Jiang, Zhong-Ping,Li, Hu,Gan, Liang-Bing,Shi, Zhang-Jie
supporting information; experimental part, p. 6002 - 6004 (2010/11/16)
Direct cross-coupling to construct sp3 C-sp3 C bonds via Fe-catalyzed benzylic C-H activation with 1-aryl vinyl acetate was developed.
Wide bite angle diphosphine rhodium complexes: Synthesis, structure, and catalytic 1,4-addition of arylboronic acids to enones
Morgan, Brad P.,Smith, Rhett C.
, p. 11 - 16 (2008/03/14)
A rhodium complex [ClRh(CO)(L1)] featuring a wide bite angle diphosphine ligand (L1 = 1,3-bis(2-diphenylphosphinomethylphenyl)benzene) has been synthesized and structurally characterized. L1 supports a bite angle (P-M-P angle, β) of 171.4° in the trans-square planar complex. L1 was tested in Rh-catalyzed 1,4-addition reactions of arylboronic acids (six examples) to α,β-unsaturated ketones (five examples). In mixed aqueous/cyclohexane solution at 60 °C, addition reactions proceed in up to quantitative yield with a 1:1 arylboronic acid/enone ratio. Yields as high as 77% can be acquired even when one of the coupling partners is sterically encumbered 2,4,6-trimethylphenylboronic acid.
