Synthesis, Characterization, and Biological Activity of Chromium Complexes as Efficient and Novel Catalysts for Direct Synthesis of Carbonyl Compounds from Benzyl/Cycloalkyl Bromides in Water under Aerobic Oxidation

الموضوعات : Iranian Journal of Catalysis

Samaa Raoof ¹ (Department of Chemical Industry, Technical Institute Mosul, Northern Technical University, Iraq)
Fadia Ahmed ² (Chemistry Department, College of Education of Pure Science, University of Mosul, Iraq)
Alyaa Al-barwari ³ (Chemistry Department, College of Education of Pure Science, University of Mosul, Iraq)
Mohanad Saleh ⁴ (Chemistry Department, College of Education of Pure Science, University of Mosul, Iraq)

تاريخ الإرسال : 13 الجمعة , جمادى الأولى, 1443 تاريخ التأكيد : 04 الإثنين , شعبان, 1443 تاريخ الإصدار : 28 الثلاثاء , رجب, 1443

الکلمات المفتاحية: Oxidation, Biological activity, Carbonyl compound, Synthesis, Chromium complex,

ملخص المقالة :

The oxidation process of benzylic halides especially benzylic bromide to corresponding carbonyl compounds such as aldehydes and ketones is a worthwhile and important organic reaction in industrial and laboratory synthetic organic chemistry. In the present study, an efficient and novel method to obtain carbonyl compounds using benzyl bromide with a catalytic amount of chromium complexes in water under aerobic conditions was reported. The six types of chromium complexes were prepared via the reaction mixture of four ligands. The prepared ligands and chromium complexes were characterized using Fourier transform spectroscopy (FT-IR), elemental analysis, molar conductivity, and magnetic moment, as well as UV-Vis spectroscopy. Different benzyl bromide derivatives were selected with both electron-donating groups and electron-withdrawing groups at –ortho, -meta, and –para positions. Under the optimum conditions, the corresponding benzaldehyde derivatives were obtained in moderate to excellent yields. In addition, the biological activity of the prepared chromium complexes was checked.

المصادر:

[1] M.J. Nejad, A. Salamatmanesh, A. Heydari, Copper (II) immobilized on magnetically separable l-arginine-β-cyclodextrin ligand system as a robust and green catalyst for direct oxidation of primary alcohols and benzyl halides to acids in neat conditions, J. Organomet. Chem., 911 (2020) 121128.

[2] S.s. Ghalehbandi, D. Ghazanfari, S.A. Ahmadi, E. Sheikhhosseini, Microwave Assisted Oxidation of Benzyl Halides to Aldehydes and Ketones with 4-Hydroxypyridinium Nitrate Functionalized Silica Gel in Aqueous Media, Org. Prep. Proced. Int., 53 (2021) 176-183.

[3] Q. Liu, M. Lu, F. Yang, W. Wei, F. Sun, Z. Yang, S. Huang, Aerobic Oxidation of Benzylic Halides to Carbonyl Compounds with Molecular Oxygen Catalyzed by TEMPO/KNO2 in Aqueous Media, Synth. Commun., 40 (2010) 1106-1114.

[4] B. Khumraksa, W. Phakhodee, M. Pattarawarapan, Rapid oxidation of organic halides with N-methylmorpholine N-oxide in an ionic liquid under microwave irradiation, Tetrahedron Lett., 54 (2013) 1983-1986.

[5] A. Kimio, A. Yoshio, O. Tetsuo, O. Fumio, APPLICATION OF BIS(p-METHOXYPHENYL)SELENOXIDE AS AN OXIDIZING AGENT OF KORNBLUM OXIDATION, Chem. Lett., 13 (1984) 891-892.

[6] G. Bratulescu, Synthesis of Aromatic Aldehydes by a Fast Method Involving Kornblum's Reaction, Synth. Commun., 38 (2008) 2748-2752.

[7] S.A. Dake, R.S. Kulkarni, V.N. Kadam, S.S. Modani, J.J. Bhale, S.B. Tathe, R.P. Pawar, Phosphonium Ionic Liquid: A Novel Catalyst for Benzyl Halide Oxidation, Synth. Commun., 39 (2009) 3898-3904.

[8] Y. He, Q. Liu, X. Ma, M. Lu, Oxidation of benzyl halides and related compounds to carbonyl compounds using hydrogen peroxide catalysed by TEMPO in water, J. Chem. Res., 37 (2013) 22-24.

[9] M. Faisal, S. Hussain, A. Haider, A. Saeed, F.A. Larik, Assessing the effectiveness of oxidative approaches for the synthesis of aldehydes and ketones from oxidation of iodomethyl group, Chem. Pap., 73 (2019) 1053-1067.

[10] S. Pradhan, V. Sharma, I. Chatterjee, Nitrosoarene-Catalyzed HFIP-Assisted Transformation of Arylmethyl Halides to Aromatic Carbonyls under Aerobic Conditions, Org. Lett., 23 (2021) 6148-6152.

[11] Y.-M. Cai, Y.-T. Xu, X. Zhang, W.-X. Gao, X.-B. Huang, Y.-B. Zhou, M.-C. Liu, H.-Y. Wu, Photoinduced Hydroxylation of Organic Halides under Mild Conditions, Org. Lett., 21 (2019) 8479-8484.

[12] S. Gambarotta, H. Alper, Phase transfer catalysis using cobalt tricarbonyl nitrosyl, J. Organomet. Chem., 212 (1981) C23-C26.

[13] M. Rosillo, G. Domínguez, J. Pérez-Castells, Chromium arene complexes in organic synthesis, Chem. Soc. Rev., 36 (2007) 1589-1604.

[14] N. Akbari, M.M. Najafpour, A chromium complex under water oxidation: A conversion mechanism and a comprehensive hypothesis, Int. J. Hydrogen Energy, 46 (2021) 3954-3963.

[15] G.J. Puzon, A.G. Roberts, D.M. Kramer, L. Xun, Formation of Soluble Organo−Chromium(III) Complexes after Chromate Reduction in the Presence of Cellular Organics, Environ. Sci. Technol., 39 (2005) 2811-2817.

[16] B.L. Small, M.J. Carney, D.M. Holman, C.E. O'Rourke, J.A. Halfen, New Chromium Complexes for Ethylene Oligomerization:  Extended Use of Tridentate Ligands in Metal-Catalyzed Olefin Polymerization, Macromolecules, 37 (2004) 4375-4386.

[17] G.C. Hargaden, P.J. Guiry, The development of the asymmetric Nozaki–Hiyama–Kishi reaction, Adv. Synth. Catal., 349 (2007) 2407-2424.

[18] A.M. Abbas, A.S. Mohammed Taib, N.H. Saeed, Synthesis and Characterization of Linear Thermally Stable polyester contain Schiff Bases, Egyptian Journal of Chemistry, 63 (2020) 2999-3013.

[19] M. Saleh, A.I. Ayoub, A.O. Hammady, Synthesis biological studies of some new heterocyclic compound derived from 2-chloro-3-formyl quinoline and 4-(benzyl sulfonyl) acetophenone, Egyptian Journal of Chemistry, 63 (2020) 4-6.

[20] Z.F. Dawood, F.J. Al-Moula, Preparation and Characterization of Cr (III) and Cu (II) Complexes With Mixed Ligand Containing Isatinazine and Semicarbazones, J. Univ. Anbar Pure Sci, 3 (2009) 21-31.

[21] R.L. Carlin, Electronic spectra of transition metal complexes, J. Chem. Educ., 40 (1963) 135.

[22] N.S. Hush, J.R. Reimers, Solvent Effects on the Electronic Spectra of Transition Metal Complexes, Chem. Rev., 100 (2000) 775-786.

[23] S.S. Jawoor, S.A. Patil, S.S. Toragalmath, Synthesis and characterization of heteroleptic Schiff base transition metal complexes: a study of anticancer, antimicrobial, DNA cleavage and anti-TB activity, J. Coord. Chem., 71 (2018) 271-283.

[24] P. Tang, Q. Zhou, S.-C. Zhang, Multiple Types of Topological Fermions in Transition Metal Silicides, Phys. Rev. Lett., 119 (2017) 206402.

[25] A. Kimio, A. Yoshio, O. Tetsuo, O. Fumio, Application of  BIS(p-methoxyphenyl)selenoxide as an oxidizing agent of Kornblum oxidation, Chem. Lett., 13 (1984) 891-892.

[26] J. Wang, Y. Zhai, Y. Wang, H. Yu, W. Zhao, Y. Wei, Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst, Dalton Trans., 47 (2018) 13323-13327.

[27] G. Shyamaprosad, J. Subrata, D. Swapan, A.A. Kumar, A Simple and Convenient Manganese Dioxide Oxidation of Benzyl Halides to Aromatic Aldehydes under Neutral Condition, Chem. Lett., 34 (2005) 194-195.

[28] B. Khumraksa, W. Phakhodee, M. Pattarawarapan, Ultrasound-assisted solventless synthesis of amines by in situ oxidation/reductive amination of benzyl halides, RSC Adv., 4 (2014) 20454-20458.