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Dergiler / NATURENGS / 2026 / Volume: 1 Issue: 1

Synthesis of New Bisbenzimidazole Salts and Determination Their Ligand Activities in C-C Coupling Reactions

Ülkü Yılmaz(Malatya Turgut Özal Üniversitesi)0000-0002-2806-4781
Hasan Küçükbay(İNÖNÜ ÜNİVERSİTESİ)0000-0002-7180-9486
Sayfa
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Yayın Tarihi
2020-06-01
DOI
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Yapay Zeka Hızlı Bakış & Çıkarımlar

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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

It was observed that remarkable ligand activities of these benzimidazolium halides (L1, L2, L3).

📌 3 Maddede Bu Makale

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Amaç & Hipotez:New bisbenzimidazole salts were synthesized with 1,4-bis(1H-benzo[d]imidazol-1-yl)butane and benzyl halides.
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Temel Bulgular & Veri:These new ligands carried out in Suzuki-Miyaura and Heck-Mizoroki C-C coupling reaction in the presence of palladium(II) acetate.
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Sonuç & Katkı:It was observed that remarkable ligand activities of these benzimidazolium halides (L1, L2, L3).
🔬Tür:Research Article
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Bisbenzimidazole · C-C coupling · Suzuki-Miyaura

Abstract

New bisbenzimidazole salts were synthesized with 1,4-bis(1H-benzo[d]imidazol-1-yl)butane and benzyl halides. These new ligands carried out in Suzuki-Miyaura and Heck-Mizoroki C-C coupling reaction in the presence of palladium(II) acetate. It was observed that remarkable ligand activities of these benzimidazolium halides (L1, L2, L3).

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Bu Makaleye Atıf Yap

Yılmaz, Ü., Küçükbay, H. (2020). Synthesis of New Bisbenzimidazole Salts and Determination Their Ligand Activities in C-C Coupling Reactions. NATURENGS, Volume: 1 Issue: 1. https://ajindex.com/articles/1532016

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Kaynakça (28)

  1. De Filippis, B., Ammazzzalorso, A., Fantacuzzi, M., Giampietro, L., Maccallini, C. and Amoroso, R. (2018). Anticancer activity of stilbene-based derivatives, Chem. Med. Chem., 12: 558-570.
  2. Shen, T., Wang, X.N. and Lou, H.X. (2009). Natural stilbenes: an overview, Nat. Prod. Rep., 26: 916-935.
  3. Kozlowski, M.C., Morgan, B.J. and Linton, E.C. (2009), Total synthesis of chiral biaryl natural products by asymmetric biaryl coupling, Chem. Soc. Rev., 38(11): 3193-3207.
  4. Littke, A.F. and Fu, G.C. (2002). Palladium-Catalyzed Coupling Reactions of Aryl Chlorides, Angew. Chem. Int. Ed., 41: 4176 -4211.
  5. N. Miyaura and A. Suzuki, A. (1995). Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds, Chem. Rev., 95(7): 2457-2483.
  6. Aktaş, A., Akkoç, S. and Gök, Y. (2013). Palladium catalyzed Mizoroki–Heck and Suzuki–Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media, J. Coord. Chem., 66(16): 2901-2909.
  7. Sajith, A.M. and Muralidharan, A. (2012). Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroarylimidazo[4,5-b]pyridines, Tetrahedron Letters, 53:1036–1041.
  8. Brenner, E., Matt, D., Henrion, M., Teci, M. and Toupet, L. (2011). Calix[4]arenes with one and two N-linked imidazolium units as precursors of N-heterocyclic carbene complexes. Coordination chemistry and use in Suzuki–Miyaura cross-coupling, Dalton Trans., 40: 9889–9898.
  9. Liu, T., Zhao, X., Shen, Q. And Lu L. (2012). General and highly efficient fluorinated-N-heterocyclic carbeneebased catalysts for the palladium-catalyzed Suzuki-Miyaura reaction, Tetrahedron, 68: 6535-6547.
  10. Wan, J-P., Wang, C., Zhou, R. and Liu, Y. (2012). Sustainable H2O/ethyl lactate system for ligand-free Suzuki–Miyaura reaction, RSC Advances, 2: 8789–8792.
  11. Heck, R. F. and Nolley, J. P. (1972). Palladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides, J. Org. Chem., 37: 2320–2322.
  12. Mizoroki, T., Mori, K., and Ozaki A. (1971). Arylation of olefin with aryl iodine catalyzed by palladium. Bull Chem Soc Jpn., 44: 581.
  13. Demir, S., Zengin, R. and Özdemir, İ. (2012). Potential N-Heterocyclic carbene precursors in the palladium catalyzed Heck reaction, Heteroatom Chem., 24(1): 77-83.
  14. Botella, L. and Najera, C. (2004). Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents, Tetrahedron, 60: 5563–5570.
  15. Du, L-H. and Wang, Y-G. (2007). Microwave-Promoted Heck Reaction Using Pd(OAc)2 as Catalyst under Ligand-Free and Solvent-Free Conditions, Synth. Commun., 37: 217–222.
  16. Fortea-Perez, F.R., Julve, M., Dikarev, E.V., Filatov, A.S. and Stiriba, S-E. (2018). Synthesis and structural characterization of well-defined bis (oxamato)palladate(II) precatalysts for Suzuki and Heck reactions, Inorg. Chim. Acta, 471: 788–796.
  17. Saikia, B., Boruah, P.R., Ali, A.A. and Sarma, D. (2015). Simple and efficient phosphine-free Pd(OAc)2 catalyzed urea accelerated Suzuki–Miyaura cross-coupling reactions in iPrOH–H2O at room temperature, Tetrahedron Letters,56: 633–635.
  18. Milde, B., Schaarschmidt, D., Rüffer, T. and Lang, H. (2012). Phosphino imidazoles and imidazolium salts for Suzuki C–C coupling reactions, Dalton Trans., 41: 5377–5390.
  19. Delaude, L. (2009). Betaine Adducts of N-Heterocyclic Carbenes: Synthesis, Properties, and Reactivity. Eur. J. Inorg. Chem. 2009: 1681–1699.
  20. Valente, C., Çalimsiz, S., Hoi, K.H., Malli, D., Sayah, M. and Organ, M.G. (2012). The development of bulky palladium NHC complexes for the most-challenging cross-coupling reactions, Angew. Chem. Int. Ed., 51: 3314 – 3332.
  21. Türkmen, H., Pelit, L. and Çetinkaya, B. (2011). Water-soluble cis-[(NHC)PdBr2(TPPTS)] catalysts and their applications in Suzuki–Miyaura coupling of aryl chlorides, J. Mol. Cat. A: Chem., 348: 88– 93.
  22. Kappe, C.O., Pieber, B. and Dallinger, D. (2013). Microwave Effects in Organic Synthesis: Myth or Reality?, Angew. Chem. Int. Ed., 52: 1088 -1094.
  23. Yılmaz, Ü., Küçükbay, H., Şireci, N., Akkurt, M., Günal, S., Durmaz, R. and Tahir, M.N. (2011). Synthesis, microwave‐promoted catalytic activity in Suzuki–Miyaura cross‐coupling reactions and antimicrobial properties of novel benzimidazole salts bearing trimethylsilyl group, Appl. Organometal. Chem., 25(5): 366-373.
  24. Yılmaz, Ü., Deniz, S., Küçükbay, H. and Şireci, N. (2013). Microwave assisted Suzuki-Miyaura and Ullmann type homocoupling reactions of 2- and 3-halopyridines using a Pd(OAc)2/benzimidazolium salt and base catalyst System, Molecules, 18(4): 3712-3724. [25] Yılmaz, Ü., Şireci, N., Deniz, S. and Küçükbay, H. (2010). Synthesis and microwave‐assisted catalytic activity of novel bis‐benzimidazole salts bearing furfuryl and thenyl moieties in Heck and Suzuki cross‐coupling reactions, Appl. Organometal. Chem., 24(5): 414-420.
  25. Yılmaz, Ü., Küçükbay, H., Çelikesir, S.T., Akkurt, M. and Büyükgüngör, O. (2013). Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc) 2, and base in a Suzuki-Miyaura reaction, Turk. J. Chem., 37: 721-733.
  26. Yılmaz, Ü. and Küçükbay, H. (2018). The catalytic effects of in situ prepared N-heterocyclic carbenes from benzimidazole salts in Suzuki–Miyaura cross-coupling reaction and uses in catalytic preparation of 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione from phenyl isocyanate, Turk. J. Chem., 42: 1706-1719.
  27. Küçükbay, H., Yılmaz, Ü., Şireci, N. and Güvenç, N. (2011). Synthesis and antimicrobial activities of some bridged bis-benzimidazole derivatives, Turk. J. Chem., 35: 561-571.
  28. Yılmaz, Ü., Küçükbay, H., Çelikesir, S.T., Akkurt, M. and Büyükgüngör, O. (2013). Synthesis of novel benzimidazole salts and microwave-assisted catalytic activity of in situ generated Pd nanoparticles from a catalyst system consisting of benzimidazol salt, Pd(OAc) 2, and base in a Suzuki-Miyaura reaction, Turk. J. Chem., 37: 721-733.