5730-92-7Relevant academic research and scientific papers
HCl-Catalyzed Aerobic Oxidation of Alkylarenes to Carbonyls
Niu, Kaikai,Shi, Xiaodi,Ding, Ling,Liu, Yuxiu,Song, Hongjian,Wang, Qingmin
, (2021/12/13)
The construction of C?O bonds through C?H bond functionalization remains fundamentally challenging. Here, a practical chlorine radical-mediated aerobic oxidation of alkylarenes to carbonyls was developed. This protocol employed commercially available HCl as a hydrogen atom transfer (HAT) reagent and air as a sustainable oxidant. In addition, this process exhibited excellent functional group tolerance and a broad substrate scope without the requirement for external metal and oxidants. The mechanistic hypothesis was supported by radical trapping, 18O labeling, and control experiments.
Catalytic reduction of nitroarenes and Suzuki-Miyaura reactions using Pd complex stabilized on the functionalized polymeric support
Ariannezhad, Maryam,Esperi, Melika,Pourmorteza, Narges,Yousefi, Abed
, (2022/02/17)
The significance of aromatic amines as crude substances in diverse applications has attracted extensive consideration in the field of economic procedures for the reduction of nitroarenes. Also, the formation of Carbon–Carbon bond as a dominant step in the structure of complex molecules is an important phenomenon in chemical reactions. Improvements of eco-friendly methodologies for reduction process and Carbon–Carbon bond formation have been noticeable. The present work represents through a capable heterogeneous Pd catalyst, the reduction of nitroarenes to the corresponding amines in the presence of N2H4 as a weak hydrogen donor reagent in the room temperature and solvent-free condition was progressed. In addition, several C–C bond formations through Suzuki-Miyaura reaction using one-pot mixture containing aryl halide, arylboronic acid in the presence of Pd catalyst at refluxed condition proceeded. Furthermore, the reusability of Pd catalyst for both reduction and Suzuki reactions showed five successive runs without any significant loss in its activity.
Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds
Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong
, p. 2134 - 2141 (2021/09/29)
A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]
A comparative study of catalytic activity on iron-based carbon nanostructured catalysts with Pd loading: Using the Box–Behnken design (BBD) method in the Suzuki–Miyaura coupling
Moniriyan, Faezeh,Sabounchei, Seyyed Javad
, (2021/09/13)
Highly dispersed palladium nanoparticles immobilized on surface-modified Fe3O4 NPs and magnetic carbon nanostructures (CNSs; carbon nanotubes/graphene oxide) were synthesized and applied as a recyclable and reusable nanocatalyst to achieve palladium (II)-catalyzed Suzuki–Miyaura reaction of arylboronic acid with aryl bromides. Carbon nanostructures with immobilized hydantoin (PH)-Pd complex display excellent stability, including a high performance at low catalyst loading. Magnetic separation prevents catalyst centrifuge or filtration and also contributes to practical techniques for recovery. Next, a response surface method based on a three-level Box–Behnken design was used, which involved three factors: catalyst loading, reaction time, and solvent. The Box–Behnken method was advantageous to parameters optimization for obtaining a yield, with high efficiency and accuracy. As a result of catalytic tests, the TONs and TOFs were calculated from all coupling reactions. The prepared nano-magnetic catalysts, after the catalysis reaction, can be easily recovered through the magnetic field. Evaluated catalytic performance indicates that these types of catalysts can function as effective recyclable catalysts at least five times without losing the initial level of catalytic activity.
A one-pot protocol for the fluorosulfonation and Suzuki coupling of phenols and bromophenols, streamlined access to biaryls and terphenyls
Hu, Rui,Li, Xinmin,Ren, Changyue,Yuan, Zeli,Zhang, Hang,Zhang, Tingting
supporting information, p. 4748 - 4753 (2020/08/17)
A one-pot protocol for the fluorosulfation and Suzuki coupling of phenols is described. The tandem reaction proceeds efficiently at room temperature, and various biaryls and biaryl fluorosulfates were obtained in good to excellent yields. Furthermore, biaryl fluorosulfates were utilized as versatile building blocks for the preparation of terphenyls. The Royal Society of Chemistry 2020.
DFT studies of the full mechanistic Suzuki–Miyaura reaction: synthesis, structural analysis and cytotoxicity of P,C-chelated palladium(II) and platinum(II) complexes
Badpa, Khadijeh,Sabounchei, Seyyed Javad,Hosseinzadeh, Leila,Gable, Robert W.
, p. 2941 - 2962 (2020/11/23)
The new Pd/Pt(II) complexes, [MBr2(Ph2PCH2PPh2C(H)C(O)C6H4-m-Br)] (M = Pd (1); M = Pt (2)), with unsymmetrical phosphorus ylide [Ph2PCH2PPh2=C(H)C(O)C6H4Br] (Y) have been synthesized through a simple procedure and were screened in a search for novel antitumor agents. These compounds were characterized by FT-IR, NMR (1H, 13C and 31P) spectroscopic methods and density functional theory methods. The crystal structures of 1 and 2 were elucidated by single-crystal X-ray diffraction. The results indicated that the complexes were P,C-chelated. Also, a theoretical study on the structure of the complexes has been investigated at the BP86/def2-SVP level of theory. The nature of metal-ligand bonds in the complexes was analyzed using EDA and ETS-NOCV analyses. In particular, a mechanistic pathway of the Suzuki–Miyaura reaction catalyzed by Pd(II) complex 1 with a P,C-donor ligand has been investigated by DFT studies, which the computational results were in agreement with those of experiments. Moreover, the cytotoxic effects of the compounds were studied in four human carcinoma cell lines: PC3, A2780, MCF-7 and PC-12 by MTT assay. Compound 1 proved to be an outstanding potent cytotoxic agent against PC3 cell line and can be considered as a promising lead in cancer drug discovery and development.
Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles
Maji, Ankur,Singh, Anshu,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik
supporting information, p. 17083 - 17096 (2019/11/26)
A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.
Different properties of P,C-donor Pd(II) and Pt(II); spectroscopic and X-ray analysis, catalytic potential and anti-proliferative potency
Yousefi, Abed,Sabounchei, Seyyed Javad,Moazzami Farida, Seyed Hamed,Karamian, Roya,Rahmani, Nosrat,Gable, Robert W.
, p. 21 - 31 (2019/04/10)
This account describes our recent studies on pallada-and platinaphosphacycle complexes with an unsymmetrical phosphonium ylide, Ph2PC(CH2)PPh2 = C(H)C(O)C6H4-p-NO2 (Y), derived from 1,1-bis(diphenylphosphino)ethylene (dppee). These complexes have been prepared through reactions between (Y) and [MCl2(cod)] (M = Pd (C1) or Pt (C2); cod = 1,5-cyclooctadiene) in equimolar ratio in the hope of finding new compounds that may be useful in stereoselective catalysis and find use as antitumor metallodrugs. Characterization of these compounds was performed by elemental analysis, IR, 1H, 13C, and 31P NMR spectroscopic methods. The structures of the Pd and Pt complexes were determined by single crystal x-ray structural analyses, showing that both complexes consist of five-membered rings formed by coordination of the phosphorus ylide (Y) through the phosphine group and the ylidic carbon atom to the metal center. The catalytic activity of the complexes, using the Mizoroki–Heck and Suzuki-Miyaura cross-coupling reactions, have been evaluated and compared. Moreover, both compounds have been found to have antitumor activity against AGS (gastric carcinoma), MCF-7 (breast carcinoma) and A549 (non-small lung carcinoma) cells with the average of IC50 values from 61.19 to 290.17 μM. Generally, C2 reveals high anticancer activity than C1.
ONO pincer palladium (II) complexes featuring furoylhydrazone ligands: Synthesis, characterization and catalytic activity towards Suzuki–Miyaura coupling reaction
Qian, Hengyu,Yu, Shuyan,Song, Liping,Zhang, Tongyan,Yin, Zhigang,Zhao, Feng,Yang, Jiale,Wang, Caihong
, (2019/08/02)
Four new palladium pincer complexes incorporating ONO type furoylhydrazone ligands have been prepared in good yields. These palladium complexes were structurally characterized by elemental analysis, infrared, 1H- and 13C-NMR spectra. X-ray single crystal analyses of Pd1–Pd4 revealed that the metal center adopted a slightly distorted square planar geometry in which the hydrazone bound the metal ion via the phenolic-O, azomethine-N and imidolate-O atoms. Using these ONO pincer complexes as catalyst, excellent yields of biaryls could be obtained for coupling of arylboronic acids with aryl bromides at a low catalyst loading (0.01?mol%).
Iridium-Catalyzed Alkene-Selective Transfer Hydrogenation with 1,4-Dioxane as Hydrogen Donor
Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 5867 - 5872 (2019/08/26)
The iridium-catalyzed transfer hydrogenation of alkenes using 1,4-dioxane as a hydrogen donor is described. The use of 1,2-bis(dicyclohexylphosphino)ethane (DCyPE), featuring bulky and highly electron-donating properties, led to high catalytic activity. A polystyrene-cross-linking bisphosphine PS-DPPBz produced a reusable heterogeneous catalyst. These homogeneous and heterogeneous protocols achieved chemoselective transfer hydrogenation of alkenes over other potentially reducible functional groups such as carbonyl, nitro, cyano, and imino groups in the same molecule.
