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Year 2019, Volume: 6 Issue: 4, 297 - 302, 31.12.2019
https://doi.org/10.17350/HJSE19030000160

Abstract

References

  • 1. Beigi Z, Kianfar AH, Farrokhpour H, Roushani M, Azarian MH, Mahmood WAK. Synthesis, characterization and spectroscopic studies of nickel(II) complexes with some tridentate ONN donor Schiff bases and their electrocatalytic application for oxidation of methanol. Journal of Molecular Liquids 249 (2018) 117–125.
  • 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 JL, Mandal P, Lai CK, 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 veMühendislik Dergisi 21 (2019) 73-82.
  • 6. Kumar SB, 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 1143 (2017) 163-167.
  • 7. Ali OAM. 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 MN, Dosi PA, Bhatt BS. 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, Kumar MD, 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. Das P, Linert W. Schiff base-derived homogeneous and heterogeneous palladium catalysts for the Suzuki–Miyaura reaction. Coordination Chemistry Reviews 311 (2016) 1–23.
  • 12. Ozdemir İ, Çetinkaya B, Demir S, Gürbüz N. Palladium-catalyzed Suzuki–Miyaura reaction using saturated N-heterocarbene ligands. Catalysis Letters 97 (2004) 37-40.
  • 13. Baran NY, Baran T, Menteş A¸ Karakışla 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 AK, Kalita RD. 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 DS, Babu SG, 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.
  • 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 crosscoupling reaction. ASEAN Journal on Science and Technology for Development 31 (2014) 15-23.
  • 17. Layek S, Anuradha, Angrahari B, 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 SuzukiMiyaura reactions. Journal of Organometallic Chemistry 846 (2017) 105-112.
  • 18. León AD, Pons J, Antón JG, Solans X, Bardia MF, 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. Polyhedron 26 (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 HMA, Saad EM, Soltan MS, Betiha MA, Butler IS, Mostafa 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. Anan NA, Hassan SM, Saad EM, Butler IS, Mostafa SI. Preparation, characterization and pH-metric measurements of 4-hydroxysalicylidenechitosan Schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II) and Au(III). Carbohydrate Research 346 (2011) 775–793.
  • 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 Chemistry 17 (2019) 571–580.
  • 24. Mohamed RG, Elantabli FM, Abdel Aziz AA, Moustafa H, El-Medani SM. 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 Structure 1176 (2019) 501-514.
  • 25. Zaghal HM, Qaseer HA. Complexes of palladium, platinum and rhodium with 2,2′-biquinoline and 2-(2′-pyridyl)quinolone. Transition Metal Chemistry16 (1991) 39–44.
  • 26. Zaghal MH, Bani Saeed MS, Abdel Hamid AAG, Ali BF. Substitution reactions of cis-dichloro(2,2 -biquinoline)palladium(II) with amino acids. Arabian Journal of Chemistry 10 (2017) S3920–S3928.

Schiff Base-Pd II Complexes Containing Pyridine and Thiophene Rings: Synthesis, Characterization, Suzuki-Miyaura C-C Coupling Reactions

Year 2019, Volume: 6 Issue: 4, 297 - 302, 31.12.2019
https://doi.org/10.17350/HJSE19030000160

Abstract

N ew 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 spectroscopic 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

References

  • 1. Beigi Z, Kianfar AH, Farrokhpour H, Roushani M, Azarian MH, Mahmood WAK. Synthesis, characterization and spectroscopic studies of nickel(II) complexes with some tridentate ONN donor Schiff bases and their electrocatalytic application for oxidation of methanol. Journal of Molecular Liquids 249 (2018) 117–125.
  • 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 JL, Mandal P, Lai CK, 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 veMühendislik Dergisi 21 (2019) 73-82.
  • 6. Kumar SB, 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 1143 (2017) 163-167.
  • 7. Ali OAM. 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 MN, Dosi PA, Bhatt BS. 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, Kumar MD, 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. Das P, Linert W. Schiff base-derived homogeneous and heterogeneous palladium catalysts for the Suzuki–Miyaura reaction. Coordination Chemistry Reviews 311 (2016) 1–23.
  • 12. Ozdemir İ, Çetinkaya B, Demir S, Gürbüz N. Palladium-catalyzed Suzuki–Miyaura reaction using saturated N-heterocarbene ligands. Catalysis Letters 97 (2004) 37-40.
  • 13. Baran NY, Baran T, Menteş A¸ Karakışla 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 AK, Kalita RD. 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 DS, Babu SG, 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.
  • 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 crosscoupling reaction. ASEAN Journal on Science and Technology for Development 31 (2014) 15-23.
  • 17. Layek S, Anuradha, Angrahari B, 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 SuzukiMiyaura reactions. Journal of Organometallic Chemistry 846 (2017) 105-112.
  • 18. León AD, Pons J, Antón JG, Solans X, Bardia MF, 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. Polyhedron 26 (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 HMA, Saad EM, Soltan MS, Betiha MA, Butler IS, Mostafa 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. Anan NA, Hassan SM, Saad EM, Butler IS, Mostafa SI. Preparation, characterization and pH-metric measurements of 4-hydroxysalicylidenechitosan Schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II) and Au(III). Carbohydrate Research 346 (2011) 775–793.
  • 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 Chemistry 17 (2019) 571–580.
  • 24. Mohamed RG, Elantabli FM, Abdel Aziz AA, Moustafa H, El-Medani SM. 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 Structure 1176 (2019) 501-514.
  • 25. Zaghal HM, Qaseer HA. Complexes of palladium, platinum and rhodium with 2,2′-biquinoline and 2-(2′-pyridyl)quinolone. Transition Metal Chemistry16 (1991) 39–44.
  • 26. Zaghal MH, Bani Saeed MS, Abdel Hamid AAG, Ali BF. Substitution reactions of cis-dichloro(2,2 -biquinoline)palladium(II) with amino acids. Arabian Journal of Chemistry 10 (2017) S3920–S3928.
There are 26 citations in total.

Details

Primary Language English
Journal Section Research Article
Authors

Kenan Buldurun This is me

Metin Ozdemir This is me

Publication Date December 31, 2019
Published in Issue Year 2019 Volume: 6 Issue: 4

Cite

Vancouver Buldurun K, Ozdemir M. Schiff Base-Pd II Complexes Containing Pyridine and Thiophene Rings: Synthesis, Characterization, Suzuki-Miyaura C-C Coupling Reactions. Hittite J Sci Eng. 2019;6(4):297-302.

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