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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Industrial production method of 4-hydroxy-1-indanone
-
, (2021/08/14)
The invention discloses an industrial production method of 4-hydroxy-1-indanone, and relates to the technical field of organic chemistry, the industrial production method comprises the following steps: taking dihydrocoumarin as a raw material, carrying out hydrolysis reaction on the dihydrocoumarin under the catalysis of hydrochloric acid to obtain an intermediate 1, and carrying out cyclization reaction on the intermediate 1 and polyphosphoric acid under the catalysis of strongly acidic resin to obtain the 4-hydroxy-1-indanone. The preparation method disclosed by the invention is short in route, easily available in raw materials, high in yield, moderate in reaction condition, suitable for industrial production, less in three wastes, more environment-friendly, easier to operate and stable in process.
Nucleophilic aromatic substitution of unactivated fluoroarenes enabled by organic photoredox catalysis
Nicewicz, David A.,Pistritto, Vincent A.,Schutzbach-Horton, Megan E.
supporting information, p. 17187 - 17194 (2020/11/02)
Nucleophilic aromatic substitution (SNAr) is a classical reaction with well-known reactivity toward electron-poor fluoroarenes. However, electron-neutral and electron-rich fluoro(hetero)arenes are considerably underrepresented. Herein, we present a method for the nucleophilic defluorination of unactivated fluoroarenes enabled by cation radical-accelerated nucleophilic aromatic substitution. The use of organic photoredox catalysis renders this method operationally simple under mild conditions and is amenable to various nucleophile classes, including azoles, amines, and carboxylic acids. Select fluorinated heterocycles can be functionalized using this method. In addition, the late-stage functionalization of pharmaceuticals is also presented. Computational studies demonstrate that the site selectivity of the reaction is dictated by arene electronics.
