126356-04-5Relevant articles and documents
Samarium metal promoted facile C-acetylation of Baylis-Hillman adducts in the presence of iron(III) chloride and iodine
Li, Shaoyu,Li, Jian,Jia, Xueshun
, p. 1115 - 1117 (2007)
A novel and efficient strategy for the C-acetylation of Baylis-Hillman adducts has been described. Promoted by Sm(0)/Ac2O/FeCl 3/I2, the present method allows for the efficient conversion of Morita-Baylis-Hillman adducts t
Metallic samarium and iodine promoted facile and efficient syntheses of trisubstituted alkenes from the acetates of Baylis-Hillman adducts
Li, Jian,Xu, Hua,Zhang, Yongmin
, p. 1931 - 1934 (2005)
Promoted by samarium metal in the presence of a catalytic amount of iodine, the Baylis-Hillman adducts underwent reductive elimination to form (E)-methylcinnamic ester derivatives. When the iodine was used in 1:1 ratio with metallic samarium, stereospecific syntheses of allylic iodide derivatives, (2Z)-2-(iodomethyl)alk-2-enoates, were achieved. Thus, this gives a new approach to the selective construction of stereo-defined trisubstituted alkenes with the simple Sm/I2 system.
Stereoselective homogeneous catalytic arylation of methyl methacrylate: Experimental and computational study
Petrovi?, Zorica D.,Petrovi?, Vladimir P.,Simijonovi?, Du?ica,Markovi?, Svetlana
, p. 144 - 151 (2012)
Catalytic systems trans-[PdCl2(DEA)2]/DEA and trans-[PdCl2(DEA)2]/[DEA][HAc], used in the model reaction of methyl methacrylate with iodobenzene, 4-iodoanisole, and bromobenzene, provide homogeneous catalysis, good regioselectivity and excellent stereoselectivity. The major product of the regioselective reaction is internal olefin. In all examined cases the only stereoisomer of the internal olefin methyl 3-phenyl-2-methylpropenoate is the E-isomer, whereas the only stereoisomer of the double arylated reaction product methyl 2-benzyl-3- phenylpropenoate is the Z-isomer. A DFT study, which investigates mechanistic aspects of migratory insertion, β-hydride elimination and reductive elimination of this phosphine-free Heck reaction, is in agreement with our experimental findings.
Finely dispersed palladium on silk-fibroin as an efficient and ligand-free catalyst for Heck cross-coupling reaction
Mirzaei, Hakimeh,Eshghi, Hossein,Seyedi, Seyed Mohammad
, (2019/09/12)
A palladium–fibroin complex (Pd/Fib.) was prepared by the addition of sonicated fibroin fiber in water to palladium acetate solution. Pd (OAc)2 was absorbed by fibroin and reduced with NaBH4 at room temperature to the Pd(0) nanoparticles. Powder-X-ray diffraction, scanning electron microscopy–energy-dispersive X-ray spectroscopy, Fourier transform-infrared, CHN elemental analysis and inductively coupled plasma-atomic emission spectroscopy were carried out to characterize the Pd/Fib. catalyst. Catalytic activity of this finely dispersed palladium was examined in the Heck coupling reaction. The catalytic coupling of aryl halides (-Cl, -Br, -I) and olefins led to the formation of the corresponding coupled products in moderate to high yields under air atmosphere. A variety of substrates, including electron-rich and electron-poor aryl halides, were converted smoothly to the targeted products in simple procedure. Heterogeneous supported Pd catalyst can be recycled and reused several times.
Synthesis of α,β-Disubstituted Acrylates via Galat Reaction
Xavier, Tania,Condon, Sylvie,Pichon, Christophe,Le Gall, Erwan,Presset, Marc
supporting information, p. 6135 - 6139 (2019/08/28)
Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.
Silica-acetylacetone-supported palladium nanoparticles as an efficient and reusable catalyst in the Heck-Mizoroki C-C cross-coupling reaction
Hajipour, Abdolreza,Shirdashtzade, Zohre,Azizi, Ghobad
, p. 143 - 146 (2015/03/30)
The preparation of palladium nanoparticles supported on acetylacetone-modified silica gel and their catalytic application for Heck olefination of aryl halides were investigated. The catalyst was characterized using X-ray diffraction, X-ray photoelectron spectroscopy, and transmission and scanning electron microscopies. The supported palladium nanoparticles are demonstrated to be a highly active and reusable catalyst for the Heck reaction. Several reaction parameters, including type and amount of solvent and base, were evaluated. The heterogeneity of the catalytic system was investigated with results indicating that there is a slight palladium leaching into the reaction solution under the applied reaction conditions. Despite this metal leaching, the catalyst can be reused nine times without significant loss of catalytic activity.
