42173-08-0Relevant academic research and scientific papers
Pyrenedione-Catalyzed α-Olefination of Nitriles under Visible-Light Photoredox Conditions
Bains, Amreen K.,Ankit, Yadav,Adhikari, Debashis
supporting information, p. 2019 - 2023 (2021/04/05)
Herein, we report a combination of pyrenedione (PD) and KOtBu to achieve facile alcohol dehydrogenation under visible-light excitation, where aerobic oxygen is utilized as the terminal oxidant. The resulting carbonyl compound can be easily converted to vinyl nitriles in a single-pot reaction, at 60 °C in 6-8 h. This environmentally benign, organocatalytic approach has distinct advantages over transition-metal-catalyzed α-olefination of nitriles, which often operate at a significantly higher temperature for an extended reaction time.
Environmentally friendly one-pot synthesis of α-alkylated nitriles using hydrotalcite-supported metal species as multifunctional solid catalysts
Motokura, Ken,Fujita, Noriaki,Mori, Kohsuke,Mizugaki, Tomoo,Ebitani, Kohki,Jitsukawa, Koichiro,Kaneda, Kiyotomi
, p. 8228 - 8239 (2007/10/03)
A ruthenium-grafted hydrotalcite (Ru/HT) and hydrotalcite-supported palladium nanoparticles (Pdnano/ HT) are easily prepared by treating basic layered double hydroxide, hydrotalcite (HT, Mg6Al 2(OH)16CO3) with aqueous RuCl 3·n H2O and K2[PdCl4] solutions, respectively, using surface impregnation methods. Analysis by means of X-ray diffraction, and energydispersive X-ray, electron paramagnetic resonance, and X-ray absorption fine structure spectroscopies proves that a monomeric RuIV species is grafted onto the surface of the HT. Meanwhile, after reduction of a surface-isolated PdII species, highly dispersed Pd nanoclusters with a mean diameter of about 70 A is observed on the Pdnano/HT surface by transmission electron microscopy analysis. These hydrotalcite-supported metal catalysts can effectively promote α-alkylation reactions of various nitriles with primary alcohols or carbonyl compounds through tandem reactions consisting of metal-catalyzed oxidation and reduction, and an aldol reaction promoted by the base sites of the HT. In these catalytic α-alkylations, homogeneous bases are unnecessary and the only by-product is water. Additionally, these catalyst systems are applicable to one-pot syntheses of glutaronitrile derivatives.
Reconstructed hydrotalcite as a highly active heterogeneous base catalyst for carbon-carbon bond formations in the presence of water
Ebitani, Kohki,Motokura, Ken,Mori, Kohsuke,Mizugaki, Tomoo,Kaneda, Kiyotomi
, p. 5440 - 5447 (2007/10/03)
The aldol reaction of carbonyl compounds is efficiently catalyzed by reconstructed hydrotalcites, obtained by treating the Mg-Al mixed oxide with water, as solid base catalysts in the presence of water. The catalysis of the reconstructed hydrotalcites is attributable to the surface base sites, created during the organization of the layered structure, with uniformly distributed strength. Furthermore, the reconstructed hydrotalcites provide a unique acid-base bifunctional surface capable of promoting the Knoevenagel and Michael reactions of nitriles with carbonyl compounds.
Direct synthesis of α,β-unsaturated nitriles in solid/liquid heterogeneous medium
Ladhar,El Gharbi
, p. 413 - 417 (2007/10/02)
α,β-unsaturated nitriles are obtained with high yields by condensation of diversely substituted aldehydes using nitriles in the presence of K2CO3. These basic active species avoids aldolisation generally observed in this type of reaction.
An Improved Cyanoalkylation Method of Aldehydes Catalyzed by Electrogenerated Base in a DMF-H2O System
Torii, Sigeru,Kawafuchi, Hiroyuki,Inokuchi, Tsutomu
, p. 2430 - 2432 (2007/10/02)
Electrogenerated base (EG base) formed in a DMF-H2O (1.85 M)-Et4NOTs (0.1-0.2 M)-(Pt) system is effective for condensation of phenylacetonitrile and its related compounds with aldehydes, giving the corresponding cyanoalkylation compounds in good yields, a
REACTIONS OF TITANIUM DERIVATIVES OF CERTAIN CH ACIDS WITH CARBONYL COMPOUNDS. II. ALDOL CONDENSATIONS WITH TITANIUM DERIVATIVES OF BENZYL CYANIDE, ISOPROPYL PHENYLACETATE, AND PHENYL BENZYL AND ETHYL BENZYL KETONES
Kasatkin, A. N.,Biktimirov, R. Kh.,Tolstikov, G. A.,Nikonenko, A. G.
, p. 1037 - 1045 (2007/10/02)
The titanium derivatives of benzyl cyanide, isopropyl phenylacetate, and phenyl benzyl and ethyl benzyl ketones, unlike the corresponding alkali-metal salts, react with aldehydes and ketones in THF at -78 to 20 deg C to form high yields of the products fr
Replacement Substituent Constants for Simple Heterocycles
Robinson, Charles N.,Wiseman, Leonard J. Jr.,Slater, Carl D.
, p. 4103 - 4112 (2007/10/02)
13C nmr absorptions are reported for the β-vinylic carbon atoms in 15 series of ethylenes bearing heterocyclic substituents.The data are used to establish the best single-parameter substituent constants, ?13, for the various heterocycles as replacements for para-substituted benzenes.Also reported are replacement dual substituent constants, including ?I and the various ?R scales needed in the Taft DSP treatment and those for F and R used in the Swain-Lupton treatment.Values of ?13, F, R, ?I, and ?Ro, respectively, for the various heterocycles as replacements for para-substituted benzenes are as follows: 2-furyl, -1.01 , 0.99, -2.51, 0.65, -0.60; 2-pyrryl, -2.53, 0.52, -5.09, -0.16, -0.62; 2-thienyl, -0.79, 2.49, -3.60, 1.82, -1.08; 3-thienyl, -0.40, 1.04, -1.57, 0.59, -0.39; 2-pyridyl, 0.88, 2.09, -0.24, 1.65, -0.45; 3-pyridyl, 0.60, 0.57, 0.63, 0.35, 0.04; and 4-pyridyl, 1.18, 1.22, 1.09, 0.92, -0.01.The DSP-NLR method of analysis is explored using electron demand parameters, ε, as determined for the vinylic side chains in para-substituted styrenes.
Side-chain Nucleophilic Reactivity of Five-membered Heterocyclic Rings: Base-catalysed Reactions of Aldehydes with Phenylacetonitrile
Alberghina, Gaetano,Amato, M. Emanuela,Fisichella, Salvatore,Pisano, Danila
, p. 295 - 298 (2007/10/02)
The rates of the sodium methoxide-catalysed condensations of heteroaromatic aldehydes (Ar=C6H5, C6H4CH3-p, C6H4OCH3-p, C6H4Cl-p, 2-thienyl, 2-furyl, pyrrol-2-yl, N-methylpyrrol-2-yl, 1-naphthyl, 3-pyridyl, 4-pyridyl) with phenylacetonitrile are measured i
1H-NMR, Ultraviolet and Infrared Spectra of Some (Z)-α-(Phenyl)-β-(2-furyl), -(2-pyrrolyl) and -(N-methyl-2-pyrrolyl)acrylonitriles
Alberghina, Gaetano,Amato, Maria Emanuela,Bottino, Francesco Agatino,Corsaro, Antonino,Fisichella, Salvatore
, p. 1747 - 1752 (2007/10/02)
The 1H-nmr data of some (Z)-α-(p-substitued-phenyl)-β-(2-furyl), -(2-pyrrolyl), and -(N-methyl-2-pyrrolyl)acrylonitriles have been investigated to indicate the preferred conformation and to establish the conformational preferences of the β-heterocyclic ri
