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    Efficient in situ N-heterocyclic carbene palladium(ii) generated from Pd(OAc)2 catalysts for carbonylative Suzuki coupling reactions of arylboronic acids with 2-bromopyridine under inert conditions leading to unsymmetrical arylpyridine ketones: synthesis, characterization and cytotoxic activities
    (Royal Soc Chemistry, 2018) Touj, Nedra; Al-Ayed, Abdullah S.; Sauthier, Mathieu; Mansour, Lamjed; Harrath, Abdel Halim; Al-Tamimi, Jamil; Ozdemir, Ismail
    N,N-Substituted benzimidazole salts were successfully synthesized and characterized by H-1-NMR, C-13 {H-1} NMR and IR techniques, which support the proposed structures. Catalysts generated in situ were efficiently used for the carbonylative cross-coupling reaction of 2 bromopyridine with various boronic acids. The reaction was carried out in THF at 110 degrees C in the presence of K2CO3 under inert conditions and yields unsymmetrical arylpyridine ketones. All N,N-substituted benzimidazole salts 2a-i and 4a-i studied in this work were screened for their cytotoxic activities against human cancer cell lines such us MDA-MB-231, MCF-7 and T47D. The N,N-substituted benzimidazoles 2e and 2f exhibited the most cytotoxic effect with promising cytotoxic activity with IC50 values of 4.45 g mL(-1) against MDA-MB-231 and 4.85 g mL(-1) against MCF7 respectively.
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    An efficient palladium catalyzed mizoroki-heck cross-coupling in water: synthesis, characterization and catalytic activities
    (Pergamon-Elsevier Science Ltd, 2024) Bensalah, Donia; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail; Gatri, Rafik; Hamdi, Naceur
    A series of new palladium complexes known as PEPPSI-type complexes 3 were successfully synthesized by reacting benzimidazolium salts 2a -e , potassium carbonate (K 2 CO 3 ), and palladium chloride (PdCl 2 ) in pyridine for 16 h at 80 degrees C. Both the benzimidazolium salts 2a -e and the resulting complexes 3 were characterized through spectroscopic data and elemental analysis. The Mizoroki-Heck coupling reaction, catalyzed by the homogeneous Pd, was effectively carried out in water without the need for any additional substances under aerobic conditions. The optimization of various key reaction parameters was performed to enhance the yield of the desired cross coupling product. The catalytic performance of these complexes in a catalytic system containing palladium complexes 3a , Et 3 N, and H 2 O was evaluated in the Mizoroki-Heck coupling reaction. The PEPPSI-type palladium complex 3a /Et 3 N/H 2 O/98 degrees C catalyst system exhibited high activity, with a turnover frequency (TOF) ranging from 12 to 14 /hour towards achieving the excellent yield of the Mizoroki-Heck coupling products for a wide range of electron withdrawing as well as electron donating aryl bromide and chlorides in shortest reaction time.
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    Palladium(ii)/N-heterocyclic carbene (NHC) catalyzed direct C-H arylation of heteroarenes with different aryl bromides and chlorides
    (Royal Soc Chemistry, 2023) Bensalah, Donia; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail; Koko, Waleed S.; Gatri, Rafik
    The growing interest of industry in the field of bi(hetero)arene compounds motivated us to synthesize these compounds via a homogeneous catalytic route using Pd PEPPSI-type complexes through direct arylation. In this study, new Pd PEPPSI-type complexes bearing NHC spectator ligands were synthesized and characterized using spectroscopic techniques, such as (HNMR)-H-1, C-13 NMR, MS spectrometry, FTIR spectroscopy and elemental analysis (PEPPSI = pyridine enhanced precatalyst preparation stabilization and initiation). All the synthesized Pd(II) complexes were stable. The catalytic properties of these complexes were evaluated in the direct C-5 mono-arylation of furan, 2-acetylthiophene and N-methylpyrrole-2-carboxaldehyde derivatives with a wide variety of (hetero)aryl halides. This environmentally attractive procedure was found to be tolerant of a wide variety of functional groups on the aryl halides and good yields were obtained in the presence of 1 mol% catalyst loading at 150 degrees C for 2 hours. In addition, the conversions for substrates containing electron-withdrawing groups were higher than those for substituents containing electron-donating groups.
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    Pd-PEPPSI-type expanded ring N-heterocyclic carbene complexes: synthesis, characterization, and catalytic activity in Suzuki-Miyaura cross coupling
    (Taylor & Francis Ltd, 2024) Alnasser, Sarah; Touj, Nedra; Alomar, Suliman; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail
    In this work, we synthesized a series of six unsymmetrical benzimidazolium salts 2 and their pyridine-enhanced precatalyst preparation stabilization and initiation (PEPPSI)-themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)]. All the products were isolated in satisfactory yields (75-85%). The synthesis of these novel palladium PEPPSI complexes involved in reacting NHC precursors with PdCl2 in pyridine at 60 degrees C in the presence of excess K2CO3. The structures of all compounds have been characterized by H-1 NMR, C-13 NMR, HRMS and IR spectroscopy, as well as elemental analysis techniques, which support the proposed structures. The catalytic activity of the six complexes was assessed in the Suzuki-Miyaura cross-coupling of phenylboronic acid and aryl halides. The reactions required only a low catalyst loading (0.1 mol%) and were carried out under mild aerobic conditions in a green, water-based solvent mixture.
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    Plausible PEPPSI catalysts for direct C-H functionalization of five-membered heterocyclic bioactive motifs: synthesis, spectral, X-ray crystallographic characterizations and catalytic activity
    (Royal Soc Chemistry, 2023) Bensalah, Donia; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail; Beji, Lotfi; Gatri, Rafik
    In this study, a series of benzimidazolium salts were synthesized as asymmetric N-heterocyclic carbene (NHC) precursors. Nine novel palladium complexes with the general formula [PdX2(NHC)(pyridine)] were synthesized using benzimidazolium salts in the PEPPSI (Pyridine Enhanced Precatalyst Preparation, Stabilization and Initiation) theme. All synthesized Pd(ii) complexes are stable. The synthesized compounds were thoroughly characterized by respective spectroscopic techniques, such as 1HNMR, 13C NMR, FTIR spectroscopy, X-ray crystallography and elemental analysis. The geometric structure of the palladium N-heterocyclic carbene has been optimized in the framework of density functional theory (DFT) using the B3LYP-D3 dispersion functional with LANL2DZ as a basis set. The on/off mechanism of pyridine assisted Pd-NHC complexes made them the best C-H functionalized catalysts for regioselective C-5 arylated products. Five membered heterocyclic compounds such as 2-acetyl furan, furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2-carboxaldehyde were treated with numerous aryl bromides and arylchlorides under optimal catalytic reaction conditions. Interestingly, all the prepared catalysts possessed essential structural features that facilitated the formation of desired coupling products in quantitative yield with excellent selectivity. The arylation reaction of bromoacetophenone was highly catalytically active with only 1 mol% catalyst loading at 150 degrees C for 2 hours. To check the efficiency of the synthesized complexes, three different five member heterocyclic substrates (2-acetylfuran, 2-acetylthiophen, 2-propylthaizole) were tested with a number of aryl bromides bearing both electron-donating and electron-withdrawing groups on para position. The data in Tables 2-4. Indicated that electron-donating groups on the para position of aryl halide decreased the catalytic conversion while electron-withdrawing groups increased the catalytic conversion this was due to the high nucleophilicity of the electron-donating substituents. In this study, a series of benzimidazolium salts were synthesized as asymmetric N-heterocyclic carbene (NHC) precursors.
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    Synthesis of palladium complexes containing benzimidazole core and their catalytic activities in direct C-H functionalization of five-membered heterocyclic bioactive motifs
    (Elsevier, 2024) Touj, Nedra; Bensalah, Donia; Mansour, Lamjed; Sauthier, Mathieu; Gurbuz, Nevin; Ozdemir, Ismail; Hamdi, Naceur
    Herein, we reported the synthesis of nine new PEPPSI-Pd(II)-N-heterocyclic carbene (NHC) complexes 3a-h containing benzimidazole core and examined their catalytic activities in the direct arylation of heteroaromatic species with aryl bromides and arylchlorides. Nine new Pd benzimidazole complexes were synthesized and their structures were elucidated by 1H and 13C NMR spectroscopy, FT-IR spectroscopy, and elemental analysis methods. In the 13C NMR spectra, NCHN peaks of Pd(II) complexes were observed between 159.7-161.5 ppm. Further, direct arylation reaction, using KOAc as base and DMAc as solvent under inert conditions, were carried out with the synthesized complexes in the presence of various aryl bromides and chlorides, and 2-acetyl furan, and furfuryl acetate 2-acetylthiophene and N-methylpyrrole-2- carboxaldehyde. Moreover, moderate to hig yields were obtained in the direct arylation of heteroarenes and aryl bromides under 1 mol% catalyst loading at 150 degrees C for 2 h loading conditions. The results showed that electron-donating and electron-withdrawing substituents on the aryl halides might produce coupling products in good yields in the presence of complexes 2a-d. Taken together, our findings are expected to contribute to the synthesis and design of palladium complexes containing benzimidazole core structures.