Antioxidant study of biaryls synthesized in the presence of Aliquat-336 activated by ultrasound

Authors

  • khemais Said Physical Organic Chemistry Laboratory (UR11ES74), Science Faculty of Sfax, 3018 Sfax,
  • Houcine Labiadh Unité de Recherche UR11ES30 de Synthèse et Structures de Nanomatériaux, Université de Carthage, Faculté des Sciences de Bizerte, 7021 Jarzouna,
  • Karima Lahbib Laboratory of Heteroatom Organic Chemistry, Faculty of Sciences of Bizerte Jarzouna 7021,
  • Ridha Ben Salem Physical Organic Chemistry Laboratory (UR11ES74), Science Faculty of Sfax, 3018 Sfax,

Abstract

In this work we describe the study of some Suzuki coupling reactions of an aryl halide with arylboronic acids. The reaction yields obtained were increased through sonochemical activation and in the presence of a phase transfer catalyst for a very short period of time. The isolated products obtained are of a high purity. In this context, we propose the reaction mechanisms for these reactions in the presence of a catalyst. Synthesized compounds were screened for theirantioxidant activity with 1,1-diphenyl-2-picrylhydrazyl (DPPH), ferric reducing power (FRP) assay and ferrous ion chelating (FIC) methods. It was found that Biaryls synthesized compounds showed appreciate antioxidant activity.

Author Biography

khemais Said, Physical Organic Chemistry Laboratory (UR11ES74), Science Faculty of Sfax, 3018 Sfax,

References

- L. Shen, S. Huang, Y. Nie, F. Lei, An Efficient Microwave-Assisted Suzuki Reaction using a New Pyridine-Pyrazole/Pd(II) Species as Catalyst in Aqueous Media, Molecules, 2013, 18, 1602-612.

- R. Narayanan, Recent Advances in Noble Metal Nanocatalysts for Suzuki and Heck Cross-Coupling

Reactions, Molecules, 2010, 15, 2124-2138.

- F. T. Luo, A. Jeevanandam, M. K. Basu, F.T. Luo and others, Efficient and High Turnover Homocoupling reaction of aryl iodide by the use of palladacycle –A convenient way to prepare poly-p-phenylene, , Tetrahedron Lett., 1998, 39, 7939.

- F. Hu, B. N. Kumpati, X. Lei, Diaminophosphine oxides as preligands for Ni-catalyzed

Suzuki cross-coupling reactions of aryl chlorides with arylboronic acids, Tetrahedron Letters,

, 55, 7215-7218.

- M. Wang, X. Yuan, H. Li, L. Ren, Z. Sun, Y. Hou, W. Chu, Nickel-catalysed Suzuki-Miyaura cross-coupling reactions of aryl halides with arylboronic acids in ionic liquids, Catalysis Communications, 2015, 58, 154-157.

- T. Zell, P. Fischer, D. Schmidt, U. Radius, C-Br Activation of Aryl Bromides at Ni0(NHC)2: Stoichiometric reactions, Catalytic Application in Suzuki-Miyaura Cross-Coupling, and Catalyst Degradation, Organometallics, 2012, 31, 5065-5073.

- C.Y. Liao, K.T. Chan, Y.C. Chang, C.Y. Chen, C.Y. Tu, C.H. Hu, H.M. Lee, Unexpected solvent-induced cis/trans isomerization and catalytic application of a bis-bidentate nickel(II) complex with N-heterocyclic carbene and amido functionalities, Organometallics, 2007, 26, 5826-5833.

- F. Alonso, I.P. Beletskaya, M. Yus, Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 1: The Heck reaction, Tetrahedron, 2005, 61, 11771-11835

- J.P. Lorimer, T.J. Mason, Sonochemistry. Part 1- the physical aspects, Chem. Soc. Rev., 1987, 16, 239-274.

- T. Lepoint, F. Mullie, What exactly is cavitation chemistry, Ultrason. Sonochem., 1994, 1, S13-S22.

- T.J. Mason, J.P. Lorimer, Applied Sonochemistry. The Uses of Power Ultrasound in Chemistry and Processing, Wiley-VCH 2002.

- M.A. Margulis, Sonochemistry as a New Promising Area of High Energy Chemistry, Chem. 2004, 38, 135-142.

- G.V. Ambulgekar, B.M. Bhanage, S.D. Samant, Low temperature recyclable catalyst for Heck reactions using ultrasound, Tetrahedron Lett., 2005, 46, 2483-2485.

- M. Atobe, Y. Kado, R. Asami, T. Fuchigami, T. Nonaka, Ultrasonic effects on electroorganic processes. Part 25. Stereoselectivity control in cathodic debromination of stilbenedibromides, Ultrason. Sonochem., 2005, 12, 1-5.

- K. Bougrin, M. Lamiri, M. Soufiaoui, Synthèse "One pot" de Dérivés Isoxazoliniques par Activation Sonochimique, Tetrahedron Lett., 1998, 39, 4455-4458.

- International Agency for Research on Cancer: Lyon. IARC Monographs on the Evaluation of the arcinogenic, Risk of Chemicals to Man" 1972, 1, 74-79.

- G.C. Porretta , R. Fioravanti, M. Biava, M. Artico, A. Villa, N. Simonetti, Antifungal agents, Part 11. Biphenyl analogues of naftifine: synthesis and antifungal activities, Arch Pharm (Weinheim), 1995, 328, 667-672.

- A. Daniel Jervis Optical brighteners: improving the colour of plastecs. Plastics, A. Jervis Optical brighteners impoving the colour of plastec, 2003, 5, 423-46.

- A. D. Hunter, D. Ristic-Petrovic, J. L. McLernon, Organometallic complexes with electronic bridges. 8. Biphenyl-, terphenyl-, naphthalene-, and anthracene-bridged bi- and trimetallic complexes of iron and chromium, Organometallics, 1992, 11, 864-871.

- K. Saïd, Y. Moussaoui, M. Kammoun, R. Ben Salem, Ultrasonic activation of Heck type reactions in the presence of Aliquat-336, Ultrasonics Sonochemistry, 2011, 18, 8-27.

- K. Saïd, Y. Moussaoui, R. Ben Salem, Heck Coupling Styrene with aryl halides Catalyzed by palladium Complexes in Biphasic Media, J. Soc. Chim. Tunisie, 2009, 11, 59-67.

- M. Oyaizu, Studies on products of the browning reaction. Antioxidative activities of browning reaction products prepared from glucosamine, Japanese Journal of Nutrition, 1986, 44, 307-315.

- A. Braca, N. D. Tommasi, L.D. Bari, C. Pizza, M. Politi, I. Morelli. Antioxidant principles from Bauhinia. Tarapotensis, J. Nat. Prod., 2001, 64, 892-895.

- M. A. Margulis, High Energ. Sonochemistry as a New Promising Area of High Energy Chemistry, Chem., 2004, 38, 135-142.

- N. Miyaura, A. Suzuki, Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds, Chem. Rev., 1995, 95, 2457-2483.

- A. Suzuki, Cross-coupling Reactions of Organoboron Compounds with Organic Halides. In: Diederich F, Stang P J, editors. Metal-Catalyzed Cross-Coupling Reactions. Weinheim, Germany: Wiley-VCH; 1998, 49-89.

- RS. R. Borhade, S. B. Waghmode, Studies on Pd/NiFe2O4 catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls, Beilstein J Org Chem., 2011, 7, 310-319.

- D. Pandiarajan , R. Ramesh, Y. Liu, R. Suresh, Palladium(II) thiosemicarbazone-catalyzed Suzuki-Miyaura cross-coupling reactions of aryl halides, Inorganic Chemistry Communications, 2013, 33, 33-37.

- L. Mhamdi, K. Saïd, Y. Moussaoui, R. Ben Salem, Biactivation de la réaction de Sonogashira par la catalyse par transfert de phase et sous irradiation ultrasonique, J. Soc. Chim. Tunisie, 2013, 15, 149-162.

- Y. Moussaoui, K. Saïd, R. Ben Salem, Anionic activation of the Wittig reaction using a solid-liquid phase transfer: examination of the medium-, temperature-, base- and phase-transfer catalyst effects, Arkivoc, 2006, xii, 1-22.

- N. Singh, P.S. Rajini, Free scavenging activity of an aqueous extract of potato pell, Food Chemistry, 2004, 85, 611-616.

- A.A El-Wakil, Synthesis, characterization, and evaluation of natural rubber-graft-N-(4-Aminodiphenyl methane) acrylamide as an antioxidant, J Appl Polym Sci, 2006, 101, 843-849.

- A. Joe Vinson, Y. Hao , X. Su, J. Agric, Phenol Antioxidant Quantity and Quality in Foods: Vegetables Food Chem., 1998, 46, 3630-3634.

- E.J. Dombrecht, P. Cos, D.V. Berghe, J.F. Van Offel, A.J. Schuerwegh, C.H. Bridts, W.J. Stevens, L.S. De lerck, Selective in vitro antioxidant properties of bisphosphonates, Biochem Biophys Res Commun., 2004, 314, 675-68

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Published

2016-05-09

Issue

Vol. 5 No. 3 (2016)

Section

Organic Chemistry

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