Schiff Base-Pd(II) Complexes Containing Pyridine and Thiophene Rings: Synthesis, Characterization, Suzuki-Miyaura C-C Coupling Reactions
New Schiff base-palladium(II) complexes (1a-d) were synthesized with the reaction of Schiff base ligand and [PdCl2(CH3CN)2]. Pd(II) complexes (1a-d) were solid and stable to moisture and air. Their structures were characterized through the spectro-scopic techniques including microanalysis, FT-IR, UV-Vis, proton (1H) and carbon (13C) NMR, mass spectrometry. The data obtained from the spectroscopic techniques showed that Schiff base-Pd(II) complexes 1a, 1b and 1c were formed through the coordination of azomethine nitrogen and carbonyl/hydroxyl oxygen atoms, while 1d complex coordinated only azomethine nitrogen atom of the Schiff base. All complexes were found to have square plane. In addition, Pd(II) complexes (1a-d) were investigated in Suzuki-Miyaura coupling reactions of different aryl bromides using phenylboronic acid. The reactions were carried out in a mixed aqueous EtOH/H2O (1/3) at room temperature with K2CO3 as the base for 1 hour. The Pd(II) complexes (1a-d) used as catalysts exhibited perfect catalytic activity in the Suzuki-Miyaura reaction.
Aryl bromides; Pd(II) complexes; Schiff base; Suzuki-Miyaura; Mass spectrometry.
2. Turan N, Buldurun K, Gündüz B, Çolak N. Synthesis and Structures of Fe(II), Zn(II) and Pd(II) Complexes with a Schiff base derived from methyl 2-amino-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate and comparison of their optical constants for different solvents and molarities. Journal of Nanoelectronics and Optoelectronics 12 (2017) 1028–1040.
3. Pratihar LJ, Mandal P, Lai KC, Chattopadhyay S. Tetradentateamidoazo Schiff base Cu(II), Ni(II) and Pd(II) complexes: Synthesis, characterization, spectral properties, and applications to catalysis in C–C coupling and oxidation reaction. Polyhedron 161 (2019) 317–324.
4. Muche S, Harms K, Biernasiuk A, Malm A, Popiołek L, Hordyjewska A, Olszewska A, Hołynska M. New Pd(II) Schiff base complexes derived from ortho-vanillin and L-tyrosine or L-glutamic acid: Synthesis, characterization, crystal structures and biological properties. Polyhedron 151 (2018) 465–477.
5. Buldurun K, Turan N, Çolak N, Özdemir İ. Schiff base and its Fe(II), Zn(II), Ru(II), Pd(II) complexes containing ONS donor atoms: synthesis, characterization and catalytic studies. Dokuz Eylül Üniversitesi Mühendislik Fakültesi Fen ve Mühendislik Dergisi 21 (2019) 73-82.
6. Kumar BS, Solanki A, Kundu S. Copper(II) and palladium(II) complexes with tridentate NSO donor Schiff base ligand: Synthesis, characterization and structures. Journal of Molecular Structure 2017 Apr; 1143: 163-167
7. Ali MAO. Characterization, thermal and fluorescence study of Mn(II) and Pd(II) Schiff base complexes. Journal of Thermal Analysis and Calorimetry 128 (2017) 1579-1590.
8. Debono N, Iglesias M, Sanchez F. New Pyridine ONN‐Pincer Gold and Palladium Complexes: Synthesis, Characterization and Catalysis in Hydrogenation, Hydrosilylation and C-C Cross‐Coupling Reactions. Advanced Synthesis & Catalysis 349 (2007) 2470-2476.
9. Patel NM, Dosi AP, Bhatt SB. Square planar palladium(II) complexes of bipyridines: Synthesis, characterization, and biological studies. Journal of Coordination Chemistry 65 (2012) 3833-3844.
10. Nandhini R, Venkatachalam G, Deepan Kumar M, Jaccob M. Dinuclear Pd(II) complexes containing bis-O,N-bidentate Schiff base ligands: Synthesis, characterization, DFT study and application as Suzuki–Miyaura coupling catalysts. Polyhedron 158 (2019) 183–192.
11. Dasa P, Linertb W. Schiff base-derived homogeneous and heterogeneous palladium catalysts for the Suzuki–Miyaura reaction. Coordination Chemistry Reviews 311 (2016) 1–23.
12. Özdemir İ, Çetinkaya B, Demir S, Gürbüz N. Palladium-catalyzed Suzuki–Miyaura reaction using saturated N-heterocarbene ligands. Catalysis Letters 97 (2004) 1–2.
13. Baran YN, Baran T, Mentes A¸ Karakıs M¸ Saçak M. Highly effective and recoverable Pd(II) catalyst immobilized on thermally stable Schiff base polymer containing phenol group: Production, characterization and application in Suzuki coupling reactions. Journal of Organometallic Chemistry 866 (2018) 87-94.
14. Kalita M, Gogoi P, Barman P, Sarma B, Buragohain KA, Kalita DR. A new series of Ni(II), Cu(II), Co(II) and Pd(II) complexes with an ONS donor Schiff base: Synthesis, crystal structure, catalytic properties and bioactivities. Polyhedron 74(2014) 93–98.
15. Priyarega S, Raja SD, Babu GS, Karvembu R, Hashimoto T, Endo A, Natarajan K. Novel binuclear palladium(II) complexes of 2-oxoquinoline-3-carbaldehyde Schiff bases: Synthesis, structure and catalytic applications. Polyhedron34 (2012)143-148.
16. Amalina MT, Hadariah B, Karimah K, Nazihah WIW. Pd(II) Complexes with Nitrogen-oxygen Donor Ligands: Synthesis, Characterization and Catalytic Activity for Suzuki-Miyaura Cross-coupling Reaction. ASEAN Journal on Science and Technology for Development 31(2014) 15-23.
17. Layek S, Anuradha BA, Pathak DD. Synthesis and characterization of a new Pd(II)-Schiff base complex[Pd(APD)2]: An efficient and recyclable catalyst for Heck-Mizoroki and Suzuki-Miyaura reactions. Journal of Organometallic Chemistry 846 (2017) 105-112.
18. León DA, Pons J, Antón GJ, Solans X, Bardia FM, Ros J. Preparation, NMR studies and crystal structure of mononuclear and dinuclear Pd(II) and Pt(II) complexes that contain 1,2-bis[3-(3,5-dimethyl-1-pyrazolyl)-2-thiapropyl]benzene. Polyhedron26 (2007) 2921-2928.
19. Agrahari B, Layek S, Anuradha, Ganguly R, Pathak DD. Synthesis, crystal structures, and application of two new pincer type palladium(II)-Schiff base complexes in C-C cross-coupling reactions. Inorganica Chimica Acta 471 (2018) 345–354.
20. Hassana AMH, Saada ME, Soltana MS, Betihab AM, Butler IS, Mostafad IS. A palladium(II) 4-hydroxysalicylidene
Schiff-base complex anchoredon functionalized MCM-41: An efficient heterogeneous catalyst for the epoxidation of olefins. Applied Catalysis A: General 488 (2014) 148–159.
21. Bon VV, Orysyk SI, Pekhnyo VI, Volkov SV. Square-planar 1:2 Ni(II) and Pd(II) complexes with different coordination mode of salicylaldehyde (4)-phenylthiosemicarbazone: Synthesis, structure and spectral properties. Journal of Molecular Structure 984 (2010) 15–22.
22. Priyarega S, Raja SD, Babu GS, Karvembu R, Hashimoto T, Endo A, Natarajan K. Novel binuclear palladium(II) complexes of 2-oxoquinoline-3-carbaldehyde Schiff bases: Synthesis, structure and catalytic applications. Polyhedron 34 (2012) 143–148.
23. Turan N, Buldurun K, Çolak N, Özdemir İ. Preparation and spectroscopic studies of Fe(II), Ru(II), Pd(II) and Zn(II) complexes of Schiff base containing terephthalaldehyde and their transfer hydrogenation and Suzuki-Miyaura coupling reaction. Open Chemistry17 (2019) 571–580.
24. Mohamed GR, Elantabli MF, Abdel Aziz AA, Moustafa H, El-Medani MS. Synthesis, characterization, NLO properties, antimicrobial, CT-DNA binding and DFT modeling of Ni(II), Pd(II), Pt(II), Mo(IV) and Ru(I) complexes with NOS Schiff base. Journal of Molecular Structure1176 (2019) 501-514.
25. Zaghal HM, Qaseer AH. Complexes of palladium, platinum and rhodium with 2,2′-biquinoline and 2-(2′-pyridyl)quinolone. Transition Metal Chemistry16 (1991) 39–44.
26. Zaghal HM, Bani Saeed SM, Hamid GAA, Ali FB. Substitution reactions of cis-dichloro(2,20-biquinoline)palladium(II) with amino acids. Arabian Journal of Chemistry 10 (2017) S3920–S3928.
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