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Suzuki-Miyaura Çapraz Eşleşme Reaksiyonunda Katalizör Olarak Heterosiklik Bileşiklerin Uygulanması

Year 2019, Volume: 40 Issue: 4, 854 - 859, 31.12.2019

Senem Akkoç

https://doi.org/10.17776/csj.613060
Cited By: 2

Abstract

Dört farklı benzimidazolyum tuzu (1-4) üç basamakta 80 oC de hazırlandı
ve yapıları spektroskopik yöntemler kullanılarak aydınlatıldı. Elde edilen
bileşikler (1-4), palladyum asetat
(PdOAc)2 ve bir baz olarak sodyum
tersiyerbütoksitin (NaOBut) varlığında iki farklı boronik
asit türevi ile farklı aril halojenürlerin karbon-karbon (C-C) bağ oluşum
reaksiyonlarında katalizör olarak in situ
ortamda test edildi. Bu reaksiyon ile dört eşleşme ürünü (5-8) %11 ile %93 arasında değişen farklı verimlerde sentezlendi. Suzuki-Miyaura
çapraz eşleşme reaksiyonunda test edilen karben öncüllerinden bileşik 2 diğerlerinden daha etkili bir
katalizör adayı olduğu bulundu.

Keywords

Suzuki-Miyaura Benzimidazol Benzimidazo

References

  • [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] 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] 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] 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] 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] 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] 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] 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] 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] 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.
  • [11] Menteşe E., Emirik M. and Sökmen B.B., Design, molecular docking and synthesis of novel 5,6-dichloro-2-methyl-1H-benzimidazole derivatives as potential urease enzyme inhibitors, Bioorg. Chem., 86 (2019)151-158.
  • [12] Babkov D.A., Zhukowskaya O.N., Borisov A.V., Babkova V.A., Sokolova E.V., Brigadirova A.A., et al., Towards multi-target antidiabetic agents: Discovery of biphenyl-benzimidazole conjugates as AMPK activators, Bioorg. Med. Chem. Lett. 29 (2019) 2443-2447.
  • [13] Mohanty S.K., Khuntia A., Yellasubbaiah N., Ayyanna C., Naga Sudha B. and Harika M.S., Design, synthesis of novel azo derivatives of benzimidazole as potent antibacterial and anti tubercular agents, Beni-Suef Uni. J. Bas. Appl. Sci. 7 (2018) 646-651.
  • [14] Fukutake T., Wada K., Yu H., Hosokawa S. and Feng Q., Development of titania-supported iridium catalysts with excellent low-temperature activities for the synthesis of benzimidazoles via hydrogen transfer, Mol. Catal. 477 (2019) 110550.
  • [15] Akkoç S., Gök Y., lhan l.Ö. and Kayser V., In situ Ggeneration of Eefficient Ppalladium N-heterocyclic Ccarbene Ccatalysts Uusing Bbenzimidazolium Ssalts for the Suzuki-Miyaura Ccross-coupling Rreaction, Curr. Org. Synth., 13 (2016) 761-766.
  • [16] Akkoç S., Özer İlhan İ., Gök Y. and Kayser V., Carbon-carbon bond formation catalyzed by PEPPSI Pd-NHC, Inorg. Chim. Acta, 461 (2017) 52-56.
  • [17] Suman G.R., Bubbly S.G., Gudennavar S.B. and Gayathri V., Benzimidazole and benzothiazole conjugated Schiff base as fluorescent sensors for Al3+ and Zn2+, J. Photochem. Photobiol., A, 382 (2019) 111947.
  • [18] Suman G.R., Bubbly S.G. and Gudennavar S.B., Benzimidazole and benzothiazole fluorophores with large Stokes shift and intense sky-blue emission in aggregation as Al3+ and Pb2+ sensors, J. Lumin. 215 (2019) 116688.
  • [19] Weissermel K. and Arpe H-J., Industrial Organic Chemistry, Weinheim. 2008.
  • [20] Akkoç S., Kayser V., İlhan İ.Ö., Hibbs D.E., Gök Y., Williams P.A., et al., New compounds based on a benzimidazole nucleus: synthesis, characterization and cytotoxic activity against breast and colon cancer cell lines, J. Organomet. Chem. 839 (2017) 98-107.
  • [21] Aslan H.G., Akkoç S., Kökbudak Z. and Aydın L., Synthesis, characterization, and antimicrobial and catalytic activity of a new Schiff base and its metal(II) complexes, J. Iran. Chem. Soc. 14 (2017) 2263-2273.

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

Year 2019, Volume: 40 Issue: 4, 854 - 859, 31.12.2019

Senem Akkoç

https://doi.org/10.17776/csj.613060
Cited By: 2

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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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.
  • [11] Menteşe E., Emirik M. and Sökmen B.B., Design, molecular docking and synthesis of novel 5,6-dichloro-2-methyl-1H-benzimidazole derivatives as potential urease enzyme inhibitors, Bioorg. Chem., 86 (2019)151-158.
  • [12] Babkov D.A., Zhukowskaya O.N., Borisov A.V., Babkova V.A., Sokolova E.V., Brigadirova A.A., et al., Towards multi-target antidiabetic agents: Discovery of biphenyl-benzimidazole conjugates as AMPK activators, Bioorg. Med. Chem. Lett. 29 (2019) 2443-2447.
  • [13] Mohanty S.K., Khuntia A., Yellasubbaiah N., Ayyanna C., Naga Sudha B. and Harika M.S., Design, synthesis of novel azo derivatives of benzimidazole as potent antibacterial and anti tubercular agents, Beni-Suef Uni. J. Bas. Appl. Sci. 7 (2018) 646-651.
  • [14] Fukutake T., Wada K., Yu H., Hosokawa S. and Feng Q., Development of titania-supported iridium catalysts with excellent low-temperature activities for the synthesis of benzimidazoles via hydrogen transfer, Mol. Catal. 477 (2019) 110550.
  • [15] Akkoç S., Gök Y., lhan l.Ö. and Kayser V., In situ Ggeneration of Eefficient Ppalladium N-heterocyclic Ccarbene Ccatalysts Uusing Bbenzimidazolium Ssalts for the Suzuki-Miyaura Ccross-coupling Rreaction, Curr. Org. Synth., 13 (2016) 761-766.
  • [16] Akkoç S., Özer İlhan İ., Gök Y. and Kayser V., Carbon-carbon bond formation catalyzed by PEPPSI Pd-NHC, Inorg. Chim. Acta, 461 (2017) 52-56.
  • [17] Suman G.R., Bubbly S.G., Gudennavar S.B. and Gayathri V., Benzimidazole and benzothiazole conjugated Schiff base as fluorescent sensors for Al3+ and Zn2+, J. Photochem. Photobiol., A, 382 (2019) 111947.
  • [18] Suman G.R., Bubbly S.G. and Gudennavar S.B., Benzimidazole and benzothiazole fluorophores with large Stokes shift and intense sky-blue emission in aggregation as Al3+ and Pb2+ sensors, J. Lumin. 215 (2019) 116688.
  • [19] Weissermel K. and Arpe H-J., Industrial Organic Chemistry, Weinheim. 2008.
  • [20] Akkoç S., Kayser V., İlhan İ.Ö., Hibbs D.E., Gök Y., Williams P.A., et al., New compounds based on a benzimidazole nucleus: synthesis, characterization and cytotoxic activity against breast and colon cancer cell lines, J. Organomet. Chem. 839 (2017) 98-107.
  • [21] Aslan H.G., Akkoç S., Kökbudak Z. and Aydın L., Synthesis, characterization, and antimicrobial and catalytic activity of a new Schiff base and its metal(II) complexes, J. Iran. Chem. Soc. 14 (2017) 2263-2273.
There are 21 citations in total.

Details

Primary Language English
Journal Section Natural Sciences
Authors

Senem Akkoç 0000-0002-1260-9425

Publication Date December 31, 2019
Submission Date August 29, 2019
Acceptance Date November 19, 2019
Published in Issue Year 2019Volume: 40 Issue: 4

Cite

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

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Investigation of structural, spectral, electronic, and biological properties of 1,3-disubstituted benzimidazole derivatives
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https://doi.org/10.1016/j.molstruc.2020.128582