36122-35-7Relevant academic research and scientific papers
A novel and efficient synthesis of maleic anhydrides by palladium-catalyzed dicarbonylation of terminal acetylenes in H2O/dioxane
Li, Jinheng,Li, Guoping,Jiang, Huanfeng,Chen, Mingcai
, p. 6923 - 6924 (2001)
Maleic anhydrides can be obtained in high yields by the PdCl2-catalyzed dicarbonylation of terminal acetylenes in H2O/dioxane. It is not necessary to add reoxidants to the reaction, but reoxidants can affect the yield and the rate. We also found that the rate decreased and only traces of maleic anhydrides were formed in the presence of KCl or LiCl.
Palladium-catalysed formation of maleic anhydrides from CO, CO2 and alk-1-ynes
Gabriele, Bartolo,Salerno, Giuseppe,Costa, Mirco,Chiusoli, Gian Paolo
, p. 1381 - 1382 (1999)
Carbon dioxide causes palladium-catalysed synthesis of unsaturated γ-lactones from alk-1-ynes and CO to shift towards maleic anhydrides.
Palladium-catalyzed dicarbonylation of terminal acetylenes: A new method for selective synthesis of unsaturated diesters and maleic anhydrides
Li,Jiang,Chen
, p. 3131 - 3134 (2001)
Maleate diesters and maleic anhydrides can be synthesized respectively by using different type of alcohol in the palladium-catalyzed dicarbonylation of terminal acetylene. In primary or second aliphatic alcohols, only α,β-unsaturated diesters were yielded. In tert-BuOH, maleic anhydrides were selectively synthesized.
Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides
Han, Zhengyu,Wang, Rui,Gu, Guoxian,Dong, Xiu-Qin,Zhang, Xumu
supporting information, p. 4226 - 4229 (2017/04/21)
Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides were hydrogenated well to provide the desired products 3-substituted succinic anhydrides in one hour with excellent results (full conversions, up to 99% yield, 99% ee, 3000 TON). Importantly, we developed a creative and efficient synthetic route to construct the key intermediate of the hypoglycemic drug mitiglinide through our catalytic system.
A dinuclear iron(II) complex bearing multidentate pyridinyl ligand: Synthesis, characterization and its catalysis on the hydroxylation of aromatic compounds
Gu, Erxing,Zhong, Wei,Ma, Hongxia,Xu, Beibei,Wang, Hailong,Liu, Xiaoming
, p. 159 - 165 (2018/03/29)
A dinuclear iron(II) complex Fe2L2(μ2-Cl)2Cl2 (L = N,N-bis(pyridin-2-ylmethyl)prop-2-yn-1-amine) was prepared and fully characterized by UV–Vis spectroscopy, elemental analysis, electrochemical analysis and X-ray single crystal diffraction analysis. The catalytic activity of the complex was assessed for the hydroxylation of aromatic compounds by using aqueous H2O2 as an oxidant in acetonitrile. The catalytic system was applicable in a wide range of substrates including aromatic compounds with both electron-donating and electron-withdrawing substituents and showed moderate to good catalytic activity and selectivity in the oxidation reactions. Particularly, in the case of benzene the selectivity of phenol achieve to 74% with the reaction conversion of 24.8%.
Discovery of pyrrolopyridazines as novel DGAT1 inhibitors
Fox, Brian M.,Iio, Kiyosei,Li, Kexue,Choi, Rebeka,Inaba, Takashi,Jackson, Simon,Sagawa, Shoichi,Shan, Bei,Tanaka, Masahiro,Yoshida, Atsuhito,Kayser, Frank
scheme or table, p. 6030 - 6033 (2010/11/05)
A new structural class of DGAT1 inhibitors was discovered and the structure-activity relationship was explored. The pyrrolotriazine core of the original lead molecule was changed to a pyrrolopyridazine core providing an increase in potency. Further exploration resulted in optimization of the propyl group at C7 and the discovery that the ester at C6 could be replaced by five-membered heterocyclic rings. The analogs prepared have DGAT1 IC 50 values ranging from >10 μM to 48 nM.
Efficient electrochemical dicarboxylations of arylacetylenes with carbon dioxide using nickel as the cathode
Yuan, Gao-Qing,Jiang, Huan-Feng,Lin, Chang
, p. 5866 - 5872 (2008/09/21)
The electrochemical dicarboxylation of arylacetylenes with carbon dioxide could be smoothly achieved in an undivided cell using Ni as the cathode and Al as the anode with n-Bu4NBr-DMF as the supporting electrolyte, at a constant current under CO2 pressure of 3 MPa and room temperature in the absence of additional catalysts. The corresponding aryl-maleic anhydrides and 2-arylsuccinic acids were afforded in excellent total yields (82-94%). Under anhydrous conditions, an unsaturated aryl-maleic anhydride as the main product was obtained, while the presence of H2O would lead to the formation of saturated 2-arylsuccinic acids. The results of cyclic voltammetric experiments show that a nickel cathode itself plays the catalytic role in the reduction reaction of arylacetylenes with CO2.
A simple, convenient method for the synthesis of maleic anhydrides from α-keto esters and alkanoic acid anhydrides using the TiCl 4/n-Bu3N reagent system
Kishorebabu, Neela,Periasamy, Mariappan
, p. 2107 - 2109 (2007/10/03)
Reaction of α-keto esters with alkanoic acid anhydrides using the TiCl4/n-Bu3N reagent system gives the corresponding maleic anhydrides in 62-95% yields.
Synthesis of maleic anhydrides and maleic acids by Pd-catalyzed oxidative dicarbonylation of alk-1-ynes
Gabriele, Bartolo,Veltri, Lucia,Salerno, Giuseppe,Costa, Mirco,Chiusoli, Gian Paolo
, p. 1722 - 1728 (2007/10/03)
We have found that carbon dioxide effectively promotes the Pd-catalyzed oxidative carbonylation of terminal alkynes to give maleic anhydrides in fair yields. Reactions were carried out in aqueous dioxane at 60-80 °C in the presence of catalytic amounts of PdI2 in conjunction with KI and under a 4:1:10 mixture of CO/air/CO2 (60 atm total pressure at 25 °C). By working in the presence of a large excess of water, maleic acids were formed selectively with unprecedented catalytic efficiencies for this kind of reaction. In the latter case, the use of an excess of carbon dioxide tended to inhibit, rather than promote, the reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Conversion of alkynes to cyclic imides and anhydrides using reactive iron carbonyls prepared from Fe(CO)5 and Fe3(CO)12
Periasamy, Mariappan,Rameshkumar, Chellappan,Mukkanti, Amere
, p. 209 - 213 (2007/10/03)
Alkyne-iron carbonyl complexes, prepared using Fe(CO)5-NaBH4-CH3COOH-amine-alkyne and Fe3(CO)12-amine-alkyne reagent systems, react with excess of amine at 25 °C to give cyclic imides in moderate to g
