1505-50-6Relevant articles and documents
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.
SYNTHESIS OF ARYLPROPIONIC ACIDS THROUGH THE α-METALLATION OF (ALKYLARENE)CHROMIUM TRICARBONYLS
Kalinin, V. N.,Udalov, N. I.,Usatov, A. V.
, p. 1550 - 1551 (1987)
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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.
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.
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.