101002-44-2Relevant articles and documents
Phosphine mono- and bis-ylide palladacycles as homogeneous molecular precatalysts: Simple and efficient protocol greatly facilitate Suzuki and Heck coupling reactions
Sabounchei, Seyyed Javad,Ahmadi, Mohsen,Panahimehr, Mohammad,Bagherjeri, Fateme Akhlaghi,Nasri, Zahra
, p. 249 - 259 (2014)
Moisture/air-stable and robust phosphine mono- and bis-ylide palladacycles as catalyst precursors were used in Suzuki and Heck cross-coupling reactions with different aryl halides including electron-rich and electron-deficient substituents. These coupling
Synthesis and structural characterization of dimeric phosphine ylide Cu(I) complexes: Application in Suzuki cross-coupling reactions and biological evaluation as antibacterial agents
Sabounchei, Seyyed Javad,Pourshahbaz, Mahbubeh,Hashemi, Ali,Ahmadi, Mohsen,Karamian, Roya,Asadbegy, Mostafa,Khavasi, Hamid Reza
, p. 111 - 119 (2014)
In this work we report the synthesis of the complexes of the type [Cu(μ-Cl){Ph2P(CH2)nPPh2C(H)C(O) PhR}]2 (n = 1: R = Cl (1), NO2 (2); n = 2: R = Cl (3), NO2 (4)) derived from the reactions of the copper(I) chloride with related phosphorus ylides in equimolar ratios using dry methanol as solvent. The identity of complex 1 was unequivocally determined by single crystal X-ray diffraction techniques, its structure consisting of five-membered rings formed by coordination of the ligands through the phosphine group and the ylidic carbon atom to the metal center. The coordination geometry around the Cu atoms in this complex can be defined as slightly distorted tetrahedral. Characterization of the obtained compounds was also performed by IR, 1H, 31P and 13C NMR spectroscopy and analytical data indicated a 1:1 stoichiometry between the Cu(I) chloride and ylide. Well-defined phosphine bis-ylide Cu(I) complexes 1 and 3 were found to be an effective catalyst for the Suzuki coupling of various aryl halides including with 4-ethyl phenylboronic acid, giving the desired coupling products at low catalyst loading in moderate to good yields. Also, the antibacterial activities of DMSO-solved complexes were measured by disc diffusion method against 6 Gram positive and negative bacteria. All Cu(I) complexes exhibited antibacterial activities against bacteria tested especially Gram negative ones.
Synthesis, X-ray structural and DFT studies of n-membered ring P, C-chelated complexes of Pd(II) and pt(II) derived from unsymmetrical phosphorus ylides and application of pd(II) complexes as catalyst in suzuki reaction
Sabounchei, Seyyed Javad,Sayadi, Mohsen,Bayat, Mehdi,Sedghi, Asiyeh,Gable, Robert W.
, p. 3727 - 3748 (2017)
The phosphonium salts [Ph2P(CH2)nPPh2CH2C(O)C6H4-m-OMe]Br (n = 1 (S1) and n = 2 (S2)) were synthesized in the reaction of bis(diphenylphosphino) methane (dppm) and bis(diphenylphosphino)ethane (dppe) with 2-bromo-3?-methoxy acetophenone, respectively. Further treatment with NEt3 gave the phosphorus ylides Ph2P(CH2)nPPh2C(H)C(O)C6H4-m-OMe (n = 1 (Y1) and n = 2 (Y2)). These ligands were treated with [MCl2(cod)] (M = Pd or Pt; cod = 1,5-cyclooctadiene) to give the P, C-chelated complexes, [MCl2(Ph2P(CH2)nPPh2C(H)C(O)C6H4-m-OMe)] (n = 1, M = Pd (3), Pt (4), and n = 2, M = Pd (5), Pt (6)). These compounds were characterized by elemental analysis, spectroscopic methods, UV–visible, and fluorescence emission spectra. Further, the structures of complexes 3 and 6 were characterized crystallographically. The palladium complexes 3 and 5 proved to be excellent catalysts for the Suzuki reactions of various aryl chlorides. Also, a theoretical study on the structure of complexes 3–6 has been investigated at the BP86/def2-SVP level of theory. The strength and nature of donor?acceptor bonds between the phosphorus ylides (L) and MCl2 fragment in the [LMCl2] (M = Pd, Pt, L = Y1, Y2) were studied by NBO and energy decomposition analysis (EDA), as well as their natural orbitals for chemical valence variation (EDA-NOCV).
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)
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.
Functionalized α-keto stabilized sulfonium ylides as highly active ligand precursors for palladium catalyzed Suzuki-Miyaura cross-couplings
Sabounchei, Seyyed Javad,Hashemi, Ali
, p. 123 - 127 (2014)
Five α-keto stabilized sulfonium ylides as type (Me) 2SCHC(O)C6H4-p-X (X = H, Br, NO2, CH3 and OCH3) {L1-L5} were used as ligand precursors in the Suzuki-Miyaura cross-coupling reaction. The best catalytic performance was obtained by using a sulfonium ylide/Pd ratio of 2:1. The catalytic systems displayed high activities, which increased in the order R = NO2 (L3) 2) 1) 3 (L4) 3 (L5). The coupling reactions proceeded smoothly with 0.05 mol% PdCl2 and 0.1 mol% L5 in DMF at 130 °C between varieties of electronically activated, deactivated and neutral aryl halides and aryl boronic acids within short reaction times and without the need for exclusion of air which gave good to high yields of the corresponding products. All the studied ligands demonstrated very high activity in the Suzuki-Miyaura cross-coupling, which yielded turnover numbers up to 1940. Comparative studies showed that the performance of sulfonium ylide L5 is significantly superior to that of related phosphine-free ligands.
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)
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.
Pallada- and platinacycle complexes of phosphorus ylides; synthesis, X-ray characterization, theoretical and electrochemical studies and application of Pd(II) complexes as catalyst in Suzuki-Miyaura coupling reaction
Sabounchei, Seyyed Javad,Sedghi, Asieh,Hashemi, Ali,Hosseinzadeh, Marjan,Bayat, Mehdi,Gable, Robert W.
, (2017)
The new unsymmetrical phosphonium salts [Ph2PCH2PPh2CH2C(O)C6H4R]Br (R= m-Br (S1) and p-CN (S2)) were synthesized in the reaction of 1,1-bis(diphenylphosphino)methane (dppm) and BrCH2C(O)C6H4R (R= m-Br and p-CN) ketones, respectively. Further treatment with NEt3 gave the α-keto stabilized phosphorus ylides Ph2PCH2PPh2C(H)C(O)C6H4R (R= m-Br (Y1) and p-CN (Y2)). These ligands were reacted with [MCl2(cod)] (M= Pd and Pt; cod= 1,5-cyclooctadiene) to give the pallada- and platinacycle complexes [MCl2(Ph2PCH2PPh2C(H)C(O)C6H4R)] (M= Pd, R= m-Br (3); R= p-CN (4) and M= Pt, R= m-Br (5); R= p-CN (6)). Cyclic voltammetry, elemental analysis, IR and NMR (1H, 13C and 31P) spectroscopic methods were used for characterization of the obtained compounds. Further, the structure of complexes 3 and 4 were characterized crystallographically. Palladacycles 3 and 4 were proved to be excellent catalysts for the Suzuki-Miyaura coupling reactions of various aryl chlorides and arylboronic acids in mixed DMF/H2O media. Also, the bonding situations between two interacted fragments [PtCl2] and Y1 and Y2 ligands in platinacycles 5 and 6 were investigated based on DFT method by using NBO, EDA and ETS-NOCV analysis.
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)
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.
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.
The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo
Zhang, Han,Yu, Peilin,Lin, Hongwei,Jin, Zefang,Zhao, Siqi,Zhang, Yi,Xu, Qingxia,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Zhang, Liangren
, p. 3976 - 3996 (2021/05/04)
The transient receptor potential melastatin 2 (TRPM2) channel is associated with ischemia/reperfusion injury, inflammation, cancer, and neurodegenerative diseases. However, the limit of specific inhibitors impedes the development of TRPM2-targeted therapeutic agents. To discover more potent and selective TRPM2 inhibitors, 59 N-(p-amylcinnamoyl) anthranilic acid (ACA) derivatives were synthesized and evaluated using calcium imaging and electrophysiology approaches. Systematic structure-activity relationship studies resulted in some potent compounds inhibiting the TRPM2 channel with sub-micromolar half-maximal inhibitory concentration values. Among them, the preferred compound A23 exhibited TRPM2 selectivity over TRPM8 and TRPV1 channels as well as phospholipase A2 and showed neuroprotective activity in vitro. Following pharmacokinetic studies, A23 was further evaluated in a transient middle cerebral artery occlusion model in vivo, which significantly reduced cerebral infarction. These data indicate that A23 might serve as a useful tool for TRPM2-related research as well as a lead compound for the development of therapeutic agents for ischemic injury.
