Research Article

Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction

Volume: 40 Number: 4 December 31, 2019
TR EN

Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction

Abstract

Four different benzimidazolium salts (1-4) were prepared in three steps at 80 oC and their structures were elucidated using spectroscopic methods. The compounds (1-4) obtained were tested in in situ medium as catalyst in the carbon-carbon (C-C) bond formation reactions of two different boronic acid derivatives with various aryl halides in the presence of palladium acetate (PdOAc)2 and sodium tertiarybutoxide (NaOBut) as a base. With this reaction, four coupling products (5-8) were synthesized in different yields ranging from 11 to 93%. Compound 2 from the carbene precursors tested in the Suzuki-Miyaura cross-coupling reaction was found to be a more effective catalyst candidate than others.

Keywords

Suzuki-Miyaura coupling reaction,Benzimidazolium salt, Catalyst

References

  1. [1] Akkoç S., Derivatives of 1-(2-(Ppiperidin-1-yl)ethyl)-1H-benzo[d]imidazole: Synthesis, Ccharacterization, Ddetermining of Eelectronic Pproperties and Ccytotoxicity Sstudies, ChemistrySelect, 4 (2019) 4938-4943.
  2. [2] Akkoç S., Kayser V. and İlhan İ.Ö., Synthesis and in vitro Aanticancer Eevaluation of Ssome Bbenzimidazolium Ssalts, J. Heterocycl. Chem. 56 (2019) 2934-2944in press.
  3. [3] Popov A.B., Stolić I., Krstulović L., Taylor M.C., Kelly J.M., Tomić S., et al., Novel symmetric bis-benzimidazoles: Synthesis, DNA/RNA binding and antitrypanosomal activity, Eur. J. Med. Chem., 173 (2019) 63-75.
  4. [4] Zaman K., Rahim F., Taha M., Ullah H., Wadood A., Nawaz M., et al., Synthesis, in vitro urease inhibitory potential and molecular docking study of Benzimidazole analogues, Bioorg. Chem. 89 (2019) 103024.
  5. [5] Sadaf H., Imtiaz ud D., Fettouhi M., Fazal A., Ahmad S., Farooqi B.A., et al., Synthesis, crystal structures and biological activities of palladium(II) complexes of benzimidazole and 2-methylbenzimidazole. Polyhedron, (2019).
  6. [6] Fang Y., Zhou H., Gu Q. and Xu J., Synthesis and evaluation of tetrahydroisoquinoline-benzimidazole hybrids as multifunctional agents for the treatment of Alzheimer's disease, Eur. J. Med. Chem., 167 (2019) 133-145.
  7. [7] Keri R.S., Rajappa C.K., Patil S.A. and Nagaraja B.M., Benzimidazole-core as an antimycobacterial agent, Pharmacol. Rep., 68 (2016)1254-1265.
  8. [8] Akkoç S., Antiproliferative activities of 2-hydroxyethyl substituted benzimidazolium salts and their palladium complexes against human cancerous cell lines, Synth. Commun., 49 (2019) 2903-2914.
  9. [9] Gök Y., Akkoç S., Çelikal Ö.Ö., Özdemir İ. and Günal S., In vitro antimicrobial studies of naphthalen-1-ylmethyl substituted silver N-heterocyclic carbene complexes, Arabian J. Chem., (2015).
  10. [10] Singh I., Luxami V. and Paul K., Effective synthesis of benzimidazoles-imidazo[1,2-a]pyrazine conjugates: A comparative study of mono-and bis-benzimidazoles for antitumor activity, Eur. J. Med. Chem. 180 (2019) 546-561.
APA
Akkoç, S. (2019). Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction. Cumhuriyet Science Journal, 40(4), 854-859. https://doi.org/10.17776/csj.613060
AMA
1.Akkoç S. Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction. CSJ. 2019;40(4):854-859. doi:10.17776/csj.613060
Chicago
Akkoç, Senem. 2019. “Application of Heterocyclic Compounds As Catalysts in Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal 40 (4): 854-59. https://doi.org/10.17776/csj.613060.
EndNote
Akkoç S (December 1, 2019) Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction. Cumhuriyet Science Journal 40 4 854–859.
IEEE
[1]S. Akkoç, “Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction”, CSJ, vol. 40, no. 4, pp. 854–859, Dec. 2019, doi: 10.17776/csj.613060.
ISNAD
Akkoç, Senem. “Application of Heterocyclic Compounds As Catalysts in Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal 40/4 (December 1, 2019): 854-859. https://doi.org/10.17776/csj.613060.
JAMA
1.Akkoç S. Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction. CSJ. 2019;40:854–859.
MLA
Akkoç, Senem. “Application of Heterocyclic Compounds As Catalysts in Suzuki-Miyaura Cross-Coupling Reaction”. Cumhuriyet Science Journal, vol. 40, no. 4, Dec. 2019, pp. 854-9, doi:10.17776/csj.613060.
Vancouver
1.Senem Akkoç. Application of Heterocyclic Compounds as Catalysts in Suzuki-Miyaura Cross-Coupling Reaction. CSJ. 2019 Dec. 1;40(4):854-9. doi:10.17776/csj.613060