Next Article in Journal
Spotlight on Biomimetic Systems Based on Lyotropic Liquid Crystal
Previous Article in Journal
What Is New in the miRNA World Regarding Osteosarcoma and Chondrosarcoma?
Article Menu
Issue 3 (March) cover image

Export Article

Open AccessArticle
Molecules 2017, 22(3), 420; doi:10.3390/molecules22030420

A Palladium Catalyst System for the Efficient Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid: Synthesis and Biological Activity Evaluation

1
Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif 2050, Tunisia
2
Laboratory of Microorganisms and Biomolecules of the Center of Biotechnology of Sfax-Tunisia, Road of Sidimansour, Km 6 B.P. 1117, Sfax 3018, Tunisia
3
Zoology Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
4
University, Faculty of Science and Art, Department of Chemistry, Malatya 44280, Turkey
5
Chemistry Department, College of Science and Arts, Qassim University, Al-Rass 51921, Saudi Arabia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 9 February 2017 / Accepted: 28 February 2017 / Published: 7 March 2017
(This article belongs to the Section Organometallic Chemistry)
View Full-Text   |   Download PDF [4150 KB, uploaded 8 March 2017]   |  

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. View Full-Text
Keywords: N-heterocyclic carbene; palladium; cross-coupling reaction; biological activities N-heterocyclic carbene; palladium; cross-coupling reaction; biological activities
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

Supplementary material

  • Externally hosted supplementary file 1
    Doi: molecules-180743

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Lamia, B.; Chakchouk-Mtibaa, A.; Hallouma, B.; Mansour, L.; Mellouli, L.; Özdemir, I.; Yaşar, S.; Hamdi, N. A Palladium Catalyst System for the Efficient Cross-Coupling Reaction of Aryl Bromides and Chlorides with Phenylboronic Acid: Synthesis and Biological Activity Evaluation. Molecules 2017, 22, 420.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top