1505-50-6Relevant academic research and scientific papers
Rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acrylic acid in water: One-step preparation of 3-arylpropionic acids
Vautravers, Nicolas R.,Breit, Bernhard
, p. 2517 - 2520 (2011)
A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium. Georg Thieme Verlag Stuttgart · New York.
Homo- and Hetero-dinuclear Arene-Linked Osmium(II) and Ruthenium(II) Organometallics: Probing the Impact of Metal Variation on Reactivity and Biological Activity
Wilson, Christopher S.,Prior, Timothy J.,Sandland, Jordon,Savoie, Huguette,Boyle, Ross W.,Murray, Benjamin S.
, p. 11593 - 11603 (2020)
Dinuclear metallodrugs offer much potential in the development of novel anticancer chemotherapeutics as a result of the distinct interactions possible with bio-macromolecular targets and the unique biological activity that can result. Herein, we describe the development of isostructural homo-dinuclear OsII–OsII and hetero-dinuclear OsII–RuII organometallic complexes formed from linking the arene ligands of [M(η6-arene)(C2O4)(PTA)] units (M=Os/Ru; PTA=1,3,5-triaza-7-phosphaadamantane). Using these complexes together with the known RuII–RuII analogue, a chromatin-modifying agent, we probed the impact of varying the metal ions on the structure, reactivity and biological activity of these complexes. The complexes were structurally characterised by X-ray diffraction experiments, their stability and reactivity were examined by using 1H and 31P NMR spectroscopy, and their biological activity was assessed, alongside that of mononuclear analogues, through MTT assays and cell-cycle analysis (HT-29 cell line). The results revealed high antiproliferative activity in each case, with cell-cycle profiles of the dinuclear complexes found to be similar to that for untreated cells, and similar but distinct profiles for the mononuclear complexes. These results indicate these complexes impact on cell viability predominantly through a non-DNA-damaging mechanism of action. The new OsII–OsII and OsII–RuII complexes reported here are further examples of a family of compounds operating via mechanisms of action atypical of the majority of metallodrugs, and which have potential as tools in chromatin research.
Photoredox Activation of Formate Salts: Hydrocarboxylation of Alkenes via Carboxyl Group Transfer
Huang, Yan,Hou, Jing,Zhan, Le-Wu,Zhang, Qian,Tang, Wan-Ying,Li, Bin-Dong
, p. 15004 - 15012 (2021/12/14)
A photoredox activation mode of formate salts for carboxylation was developed. Using a formate salt as the reductant, carbonyl source, and hydrogen atom transfer reagent, a wide range of alkenes can be converted into acid products via a carboxyl group tra
Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions
El Ali, Bassam,Fettouhi, Mohammed,Iali, Wissam,Mansour, Waseem,Suleiman, Rami
, (2021/08/09)
A series of three 1,3-propanediyl bridged bis(N-heterocyclic carbene)palladium(II) complexes (Pd-BNH1, Pd-BNH2, and Pd-BNH3), with + I effect order of the N-substituents of the ligand (isopropyl > benzyl > methoxyphenyl), was the subject of a spectroscopic, structural, computational and catalytic investigation. The bis(NHC)PdBr2 complexes were evaluated in Mizoroki-Heck coupling reactions of aryl bromides with styrene or acrylate derivatives and showed high catalytic efficiency to produce diarylethenes and cinnamic acid derivatives. The X-ray structure of the most active palladium complex Pd-BNH3 shows that the Pd(II) center is bonded to the two carbon atoms of the bis(N-heterocyclic carbene) and two bromide ligands in cis position, resulting in a distorted square planar geometry. The NMR data of Pd-BNH3 are consistent with a single chair-boat rigid conformer in solution with no dynamic behavior of the 8-membered ring palladacycle in the temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated softness, in the case of Pd-BNH3, is expected to favor the coordination steps of both the soft aryl bromides and alkenes in the Heck catalytic cycle.
Synthesis method of succinic acid derivative or 3 -arylpropionic acid (by machine translation)
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Paragraph 0101-0114; 0115; 0119, (2020/10/30)
The invention discloses a synthesis method of a succinic acid derivative or 3 -arylpropionic acid, which comprises the following steps: adding a base in a drying reaction tube and CO removing CO. 2 The reaction is carried out under the irradiation of visible light, the reaction is carried out under visible light irradiation, and then separation and purification are carried out to obtain the butanedioic acid derivative or 3 -arylpropionic acid product; the base comprises sodium tert-butoxide, potassium tert-butoxide, lithium tert-butyl alcohol and 4 - potassium carbonate; and the reaction substrate comprises an acrylate compound or an aryl vinyl compound. CO can be induced by visible light. 2 The scheme provided by the invention is mild in reaction condition and wide in reaction 3 - substrate selectivity, and the reaction substrate is wide in selectivity, the raw materials are cheap and easily available, and the method has a good industrial application prospect. (by machine translation)
Generalized Chemoselective Transfer Hydrogenation/Hydrodeuteration
Wang, Yong,Cao, Xinyi,Zhao, Leyao,Pi, Chao,Ji, Jingfei,Cui, Xiuling,Wu, Yangjie
supporting information, p. 4119 - 4129 (2020/08/10)
A generalized, simple and efficient transfer hydrogenation of unsaturated bonds has been developed using HBPin and various proton reagents as hydrogen sources. The substrates, including alkenes, alkynes, aromatic heterocycles, aldehydes, ketones, imines, azo, nitro, epoxy and nitrile compounds, are all applied to this catalytic system. Various groups, which cannot survive under the Pd/C/H2 combination, are tolerated. The activity of the reactants was studied and the trends are as follows: styrene'diphenylmethanimine'benzaldehyde'azobenzene'nitrobenzene'quinoline'acetophenone'benzonitrile. Substrates bearing two or more different unsaturated bonds were also investigated and transfer hydrogenation occurred with excellent chemoselectivity. Nano-palladium catalyst in situ generated from Pd(OAc)2 and HBPin extremely improved the TH efficiency. Furthermore, chemoselective anti-Markovnikov hydrodeuteration of terminal aromatic olefins was achieved using D2O and HBPin via in situ HD generation and discrimination. (Figure presented.).
Method for selective reduction α, β - unsaturated carbonyl compound carbon-carbon double bond (by machine translation)
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Paragraph 0035-0038, (2020/06/17)
The invention discloses a method for selectively reducing carbon-carbon double bonds in α and β - unsaturated carbonyl compounds, which comprises the following steps of adding α, β - unsaturated carbonyl compounds shown in formula (I) in an electrolysis system and reducing α and β - unsaturated carbonyl compounds with carbonyl-conjugated carbon-carbon double bonds through an electrochemical cathodic reduction reaction. Compared with the reported method, the method disclosed by the invention does not use a metal catalyst and an external oxidant; and the reaction raw material and the electrolyte are low in price, nontoxic and tasteless, simple and convenient in post-treatment. (by machine translation)
Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins
Alkayal, Anas,Buckley, Benjamin R.,Malkov, Andrei V.,Montanaro, Stephanie,Tabas, Volodymyr,Wright, Iain A.
supporting information, (2020/02/13)
The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.
Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions
Gevorgyan, Ashot,Hopmann, Kathrin H.,Bayer, Annette
, p. 2080 - 2088 (2020/02/20)
A range of hitherto unexplored biomass-derived chemicals have been evaluated as new sustainable solvents for a large variety of CO2-based carboxylation reactions. Known biomass-derived solvents (biosolvents) are also included in the study and the results are compared with commonly used solvents for the reactions. Biosolvents can be efficiently applied in a variety of carboxylation reactions, such as Cu-catalyzed carboxylation of organoboranes and organoboronates, metal-catalyzed hydrocarboxylation, borocarboxylation, and other related reactions. For many of these reactions, the use of biosolvents provides comparable or better yields than the commonly used solvents. The best biosolvents identified are the so far unexplored candidates isosorbide dimethyl ether, acetaldehyde diethyl acetal, rose oxide, and eucalyptol, alongside the known biosolvent 2-methyltetrahydrofuran. This strategy was used for the synthesis of the commercial drugs Fenoprofen and Flurbiprofen.
Preparation method for synthesizing propiolic acid and derivatives thereof
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Paragraph 0015, (2020/10/14)
The invention provides a preparation method for synthesizing propiolic acid and derivatives thereof. The synthetic route of the method comprises the following steps: firstly, under anhydrous and anaerobic conditions, adding magnesium metal, elemental iodine and a solvent into a reactor, uniformly stirring the reactants, and then dropwise adding halogenated hydrocarbon to react to generate a hydrocarbyl magnesium halide Grignard reagent; dropwise adding terminal alkyne into the reactor for Grignard exchange reaction to obtain alkynyl magnesium halide; and finally, introducing CO2 into the reactor, carrying out nucleophilic addition reaction, and hydrolyzing the product to obtain the propiolic acid compound. The preparation method provided by the invention is simple, safe and mild in operation condition.
