119-84-6Relevant articles and documents
Hydrogenation of coumarin to octahydrocoumarin over a Ru/C catalyst
Bílková, Dana,Jansa, Petr,Paterová, Iva,?erveny, Libor
, p. 957 - 960 (2015)
The production of octahydrocoumarin, which can serve as a replacement for toxic coumarin, was investigated using 5% Ru on active carbon (Ru/C) as the catalyst for the hydrogenation of coumarin. The hydrogenation was studied by optimizing the reaction conditions (pressure, solvent and coumarin concentration). The activity and selectivity of the Ru/C catalyst were compared for different solvents. The mechanism of coumarin hydrogenation was deduced. The formation of side products was explained. The optimal hydrogenation reaction conditions were: 130 °C, 10 MPa, 60 wt% coumarin in methanol, and 0.5 wt% (based on coumarin) of Ru/C catalyst. At the complete conversion of coumarin, the selectivity to the desired product was 90%.
Cerium-Catalyzed Hydrosilylation of Acrylates to Give α-Silyl Esters
Pindwal, Aradhana,Patnaik, Smita,Everett, William C.,Ellern, Arkady,Windus, Theresa L.,Sadow, Aaron D.
, p. 628 - 631 (2017)
The homoleptic organocerium complex Ce{C(SiHMe2)3}3(1) reacts with B(C6F5)3to produce the zwitterionic bis(alkyl) hydridoborato Ce{C(SiHMe2)3}2HB(C6F5)3(2). NMR and IR spectroscopy and X-ray crystallography indicate that each alkyl ligand contains two bridging Ce?H-Si interactions in both 1 and 2. Compound 2 serves as a precatalyst for the hydrosilylation of acrylates to give α-silyl esters at room temperature with a turnover number of 2200.
Synthesis of 6-, 7-, and 8-membered lactones via the nickel-catalysed electrochemical arylation of electron-deficient olefins
De Mendon?a Cavalcanti, Janesmar Camilo,Fonseca Goulart, Marilia Oliveira,Léonel, Eric,Nédélec, Jean-Yves
, p. 6343 - 6345 (2002)
A nickel-catalysed electroreductive process of arylation of α,β-unsaturated carboxylic esters has been applied to the synthesis of medium-sized lactones. Of the two possible approaches investigated in this study, the most efficient one involves first the electrochemical condensation, followed by the lactonisation.
Palladium nanoparticles stabilised by PTA derivatives in glycerol: Synthesis and catalysis in a green wet phase
Chahdoura, Faouzi,Favier, Isabelle,Pradel, Christian,Mallet-Ladeira, Sonia,Gómez, Montserrat
, p. 47 - 51 (2015)
Palladium nanoparticles stabilised by N-substituted 1,3,5-triaza-7-phosphaadamantane ionic ligands were synthesised from Pd(II) precursors and characterised in neat glycerol, observing an important effect of the phosphine nature in the dispersion of the nanoclusters in solution. The most homogeneously dispersed nanoparticles (Pd1a) led to the best catalytic behaviour in the benchmark Suzuki-Miyaura reaction. From this screening, Pd1a was applied in different CC cross-couplings and hydrogenation reactions, isolating the expected products in high yields (> 90%). An efficient catalyst immobilisation in glycerol was attained (up to ten runs without any sign of activity loss).
Heterogeneous Baeyer-Villiger oxidation of ketones using m- chloroperbenzoic acid catalyzed by hydrotalcites
Kaneda, Kiyotomi,Yamashita, Toyokazu
, p. 4555 - 4558 (1996)
Hydrotalcites promote the Baeyer-Villiger oxidation of various ketones using m-chloroperbenzoic acid to give high yields of lactones and esters.
SmI2 mediated Barbier reaction of α-fluoro ethers
Ringom, Rune,Benneche, Tore
, p. 121 - 122 (1999)
Addition of α-fluoro ethers to cyclohexanone in THF at ambient temperature has been mediated by means of SmI2.
Tetrahedral Intermediate in Acyl Transfer Reactions. A Revaluation of the Significance of Rate Data Used in Deriving Fundamental Linear Free Energy Relationships
DeTar, DeLos F.
, p. 7205 - 7212 (1982)
A theoretical investigation of model mechanisms applicable to acyl transfer reactions in solution has shown that the interpretations of experimental rate constants in terms of mechanistic constants are all subject to an ambiguity that is well-known in principle but usually ignored or incorrectly evaluated in practice.For all models involving reversibly formed tetrahedral intermediates, the experimental constants are products of the form kffp in which kf is equal to ki+>n or to ki and fp is a product distribution fraction.Each assesible pH range can give a maximum of one constant that depends on the pH; there is no way to dissect out the desired mechanistic constants or the equilibrium constants for several tetrahedral intermediates unless some independent means can be developed to measure the fp.These conclusions are of major concern to all studies that attempt to relate reactivity to structure.Representative acyl transfer reactions have been reinterpreted.One example of the so-called trialkyl lock acceleration is now shown to amount to a factor of about 4000 for the mechanistic rates in contrast to the factor of 5*1010 originally proposed.Most of the decrease in estimate arises from recent reevaluations on observed rates, but there is a further decrease by a factor of 100 in the mechanistic rates due to considerations treated in present study.Evidence is also presented that certain acyl transfer reactions in solution may proceed by direct displacement rather than though a reversibly formed tetrahedral intermediate.
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Sato et al.
, p. 2971 (1964)
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Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer
Larionova, Natalia A.,Ondozabal, Jun Miyatake,Cambeiro, Xacobe C.
supporting information, p. 558 - 564 (2020/12/07)
Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).
Hydrogenation reaction method
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Paragraph 0034; 0209-0212, (2020/05/14)
The invention relates to a hydrogenation reaction method, and belongs to the technical field of organic synthesis. The hydrogenation reaction method provided by the invention comprises the following steps: carrying out a hydrogen transfer reaction on a hydrogen acceptor compound, pinacol borane and a catalyst in a solvent in the presence of proton hydrogen, so that the hydrogen acceptor compound is subjected to a hydrogenation reaction; the catalyst is one or more than two of a palladium catalyst, an iridium catalyst and a rhodium catalyst; the hydrogen acceptor compound comprises one or morethan two functional groups of carbon-carbon double bonds, carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogentriple bonds and epoxy. The method is mild in reaction condition, easy to operate, high in yield, short in reaction time, wide in substrate application range, suitable for carbon-carbon double bonds,carbon-carbon triple bonds, carbon-oxygen double bonds, carbon-nitrogen double bonds, nitrogen-nitrogen double bonds, nitryl, carbon-nitrogen triple bonds and epoxy functional groups, good in selectivity and high in reaction specificity.