title: A Palladium Catalyst System for the Efficient Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid: Synthesis and Biological Activity Evaluation.
abstract: New benzimidazolium salts 1a-c and their palladium bis-N-heterocyclic carbene complexes 2a-c and palladium PEPPSI-type complexes 3a-c were designed, synthesized and structurally characterized by NMR (1H and 13C), IR, DART-TOF mass spectrometry and elemental analysis. Then these complexes 2-3 were employed in the Suzuki-Miyaura cross-coupling reaction of substituted arenes with phenylboronic acid under mild conditions in toluene and DMF/H2O (1/1) to afford functionalized biaryl derivatives in good to excellent yields. The antibacterial activity of palladium bis-N-heterocyclic carbene complexes 2a-c and palladium PEPPSI-type complexes 3a-c was measured by disc diffusion method against Gram positive and Gram negative bacteria. Compounds 2a, 2c and 3a-c exhibited potential antibacterial activity against four bacterial species among the five used indicator cells. The product 2b inhibits the growth of the all five tested microorganisms. Moreover, the antioxidant activity determination of these complexes 2-3, using 2.2-diphenyl-1-picrylhydrazyl (DPPH) as a reagent, showed that compounds 2a-c and 3b possess DPPH antiradical activity. The higher antioxidant activity was obtained from the product 2b which has radical scavenging activity comparable to that of the two used positive controls (gallic acid "GA" and tutylatedhydroxytoluene "BHT"). Investigation of the anti-acetylcholinesterase activity of the studied complexes showed that compounds 2b, 3a, and 3b exhibited moderate activity at 100 μg/mL and product 2b is the most active.
authors.affiliation: Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia. boubakri_lamia@yahoo.co.uk.
authors.forename: Boubakri
authors.initials: B
authors.lastname: Lamia
authors.affiliation: Laboratory of Microorganisms and Biomolecules of the Center of Biotechnology of Sfax-Tunisia, Road of Sidimansour, Km 6 B.P. 1117, Sfax 3018, Tunisia.
authors.forename: Ahlem
authors.initials: A
authors.lastname: Chakchouk-Mtibaa
authors.affiliation: Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia. bilelhallouma@gmail.com.
authors.forename: Bilel
authors.initials: B
authors.lastname: Hallouma
authors.affiliation: Zoology Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia. lamjed.mansour@gmail.com.
authors.forename: Lamjed
authors.initials: L
authors.lastname: Mansour
authors.affiliation: Laboratory of Microorganisms and Biomolecules of the Center of Biotechnology of Sfax-Tunisia, Road of Sidimansour, Km 6 B.P. 1117, Sfax 3018, Tunisia. lotfi.mallouli@cbs.rnrt.tn.
authors.forename: Lotfi
authors.initials: L
authors.lastname: Mellouli
authors.affiliation: University, Faculty of Science and Art, Department of Chemistry, Malatya 44280, Turkey. iozdemir44@gmail.com.
authors.forename: Ismail
authors.initials: I
authors.lastname: Özdemir
authors.affiliation: University, Faculty of Science and Art, Department of Chemistry, Malatya 44280, Turkey. syasar44@gmail.com.
authors.forename: Sedat
authors.initials: S
authors.lastname: Yaşar
authors.affiliation: Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia. naceur.hamdi@isste.rnu.tn.|Chemistry Department, College of Science and Arts, Qassim University, Al-Rass 51921, Saudi Arabia. naceur.hamdi@isste.rnu.tn.
authors.forename: Naceur
authors.initials: N
authors.lastname: Hamdi
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D001897:Boronic Acids / Q000138:chemical synthesis* / Q000494:pharmacology*; D001965:Bromides / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D002800:Cholinesterase Inhibitors / Q000737:chemistry / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010165:Palladium / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001897:Boronic Acids; D001965:Bromides; D002712:Chlorides; D002800:Cholinesterase Inhibitors; D010165:Palladium; C010686:benzeneboronic acid
keywords: N-heterocyclic carbene; biological activities; cross-coupling reaction; palladium