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4-Vynilbenzil Grubu Taşıyan Benzimidazol Fonksiyonelleştirilmiş PEPPSI tipi Pd(II)NHC Komplekslerinin Dizaynı, Sentezi, Karakterizasyonu ve Doğrudan Arilasyon Reaksiyonundaki Katalitik Aktivitesi

Year 2022, Issue: 40, 7 - 14, 30.09.2022

Semra Daşgın Yetkin Gök Aydın Aktaş

https://doi.org/10.31590/ejosat.1168351

Abstract

Bu çalışma, 4-vinilbenzil grubunu içeren bir dizi benzimidazol fonksiyonelli PEPPSI (PEPPSI, Pyridine Enhanced Precatalyst Preparation Stabilization, and Initiation) tipi Pd(II)NHC (NHC, N-heterocyclic Carbene) kompleksinin sentezini ve karakterizasyonunu içerir. Bu kompleksler 4-vinilbenzil grubu taşıyan benzimidazolyum tuzları, paladyum klorür (PdCl2), baz olarak potasyum karbonat (K2CO3) ve 3-kloropiridinden sentezlendi. Tüm komplekslerin yapıları 1H NMR, 13C NMR ve FTIR spektroskopik teknikleri kullanılarak karakterize edildi. Karkterizasyon sonucu elde edilen veriler önerilen formüller ile tutarlıydı. Özellikle NMR spektrumlarında başlangıç materyali olarak kullanılan 4-vinilbenzil grubu taşıyan benzimidazolyum tuzlarına ait karakteristik proton ve karbon piklerinin gözlenmemesi, bunu yerine benzimidazolyum ligandının palladyum metaline koordinasyonu sonucu karbon NMR spektrumunda daha düşük alanda karben piklerinin varlığı komplekslerin oluşumunu kanıtlamaktadır. Ayrıca, tüm 4-vinil benzil grubu içeren benzimidazolyum fonsiyonelli PEPPSI tipi Pd(II)NHC komplekslerinin doğrudan arilasyon tepkimelerindeki katalitik aktiviteleri incelenmiştir. Aril bromürlerin, furan ve tiofen türevi bileşikler ile tepkimelerinde katalizör olarak kullanılan tüm komplekslerin bu reaksiyonlarda orta ve yüksek derecede aktif katalizörler oldukları görülmüştür.

Keywords

Doğrudan arilasyon Katalizör N-heterosiklik karben Palladyum PEPPSI

Supporting Institution

İnönü Üniversitesi BAP birimi

Project Number

İUBAP: 2015/10

Thanks

Bu çalışma İnönü Üniversitesi (Türkiye) Bilimsel Araştırma Projeleri Birimi tarafından finansal olarak desteklenmiştir (İUBAP: 2015/10). Yazarlar, bileşiklerin karakterizasyonu için İnönü Üniversitesi Fen Fakültesi Kimya Bölümü'ne teşekkür eder.

References

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  • Aktaş, A., Celepci, D. B., Gök, Y., & Aygün, M. (2018). 2‐Hydroxyethyl‐Substituted Pd‐PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki‐Miyaura Reaction for Aryl Chlorides in Aqueous Media. ChemistrySelect, 3(35), 9974-9980.
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  • Arduengo III, A. J., Goerlich, J. R., Krafczyk, R., & Marshall, W. J. (1998). 1, 3, 4, 5‐Tetraphenylimidazol‐2‐ylidene: The Realization of Wanzlick's Dream. Angewandte Chemie International Edition, 37(13‐14), 1963-1965.
  • Arıcı, H., Sündü, B., Fırıncı, R., Ertuğrul, E., Özdemir, N., Cetinkaya, B., ... & Günay, M. E. (2021). The synthesis of new PEPPSI-type N-heterocyclic carbene (NHC)-Pd (II) complexes bearing long alkyl chain as precursors for the synthesis of NHC-stabilized Pd (0) nanoparticles and their catalytic applications. Journal of Organometallic Chemistry, 934, 121633.
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  • Herrmann, W. A. (2002). N‐heterocyclic carbenes: a new concept in organometallic catalysis. Angewandte Chemie International Edition, 41(8), 1290-1309.
  • Herrmann, W. A., Schütz, J., Frey, G. D., & Herdtweck, E. (2006). N-heterocyclic carbenes: synthesis, structures, and electronic ligand properties. Organometallics, 25(10), 2437-2448.
  • Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014). An overview of N-heterocyclic carbenes. Nature, 510(7506), 485-496.
  • İmik, F., Yaşar, S., & Özdemir, İ. (2019). Synthesis and investigation of catalytic activity of phenylene–And biphenylene bridged bimetallic Palladium-PEPPSI complexes. Journal of Organometallic Chemistry, 896, 162-167.
  • Jiao, L. Y., Yin, X. M., Liu, S., Zhang, Z., Sun, M., & Ma, X. X. (2020). 1, 2, 3-Triazol-5-ylidene bearing a pyridine auxiliary based bidentate PEPPSI type palladium (II) complex: Synthesis, structure, and application in the direct arylation of pyridine N-oxide. Catalysis Communications, 135, 105889.
  • Kim, D., Choi, G., Kim, W., Kim, D., Kang, Y. K., & Hong, S. H. (2021). The site-selectivity and mechanism of Pd-catalyzed C (sp 2)–H arylation of simple arenes. Chemical science, 12(1), 363-373.
  • Lvov, A. G., Khusniyarov, M. M., & Shirinian, V. Z. (2018). Azole-based diarylethenes as the next step towards advanced photochromic materials. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 36, 1-23.
  • Mao, S., Shi, X., Soulé, J. F., & Doucet, H. (2020). Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst. European Journal of Organic Chemistry, 2020(1), 91-97.
  • Mishra, K., & Lee, Y. R. (2019). Highly synergistic effect of bifunctional Ru-rGO catalyst for enhanced hydrogenative-reductive benzylation of N-heteroaromatics. Journal of Catalysis, 376, 77-86.
  • O’Brien, C. J., & Kantchev, E. A. B. (2006). C. 35 Valente, N. Hadei, GA Chass, A. Lough, AC Hopkinson and M. G. Organ. Chem. Eur. J, 12, 4743.
  • Organ, M. G., Chass, G. A., Fang, D. C., Hopkinson, A. C., & Valente, C. (2008). Pd-NHC (PEPPSI) complexes: Synthetic utility and computational studies into their reactivity. Synthesis, 2008(17), 2776-2797.
  • Öfele, K. (1968). 1, 3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer Übergangsmetall-carben-komplex. Journal of Organometallic Chemistry, 12(3), P42-P43.
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  • Reddy, M. V. K., Anusha, G., & Reddy, P. V. G. (2020). Sterically enriched bulky 1, 3-bis (N, N′-aralkyl) benzimidazolium based Pd-PEPPSI complexes for Buchwald–Hartwig amination reactions. New Journal of Chemistry, 44(27), 11694-11703.
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Design, Synthesis, Characterization and Catalytic Activity in Direct Arylation Reaction of the Benzimidazole-Functionalized PEPPSI-type Pd(II)NHC Complexes bearing 4-Vynylbenzyl Group

Year 2022, Issue: 40, 7 - 14, 30.09.2022

Semra Daşgın Yetkin Gök Aydın Aktaş

https://doi.org/10.31590/ejosat.1168351

Abstract

This study includes the synthesis and characterization of a series of benzimidazole functional PEPPSI (PEPPSI, Pyridine Enhanced Precatalyst Preparation Stabilization, and Initiation) type Pd(II)NHC (NHC, N-heterocyclic Carbene) complexes containing the 4-vinylbenzyl group. These complexes were synthesized from benzimidazolium salts bearing 4-vinylbenzyl group, palladium chloride (PdCl2), potassium carbonate (K2CO3) and 3-chloropyridine as a base. The structures of all complexes were characterized using 1H NMR, 13C NMR, and FTIR spectroscopic techniques. The data obtained from characterization were consistent with the proposed formulas. In particular, the absence of characteristic proton and carbon peaks of benzimidazolium salts with 4-vinylbenzyl group used as starting material in NMR spectra, instead of the coordination of benzimidazolium ligand to palladium metal, the presence of carbene peaks in the downfield of the carbon NMR spectrum proves the formation of complexes. In addition, the catalytic activities of all PEPPSI type Pd(II)NHC complexes with benzimidazolium functionalities containing 4-vinylbenzyl groups in direct arylation reactions were investigated. All complexes used as catalysts in the responses of aryl bromides with furan and thiophene derivative compounds were found to be moderately and highly active catalysts in these reactions.

Keywords

Catalyst Direct arylation N-heterocyclic carbene Palladium PEPPSI

Project Number

İUBAP: 2015/10

References

  • Abbot, V., Sharma, P., Dhiman, S., Noolvi, M. N., Patel, H. M., & Bhardwaj, V. (2017). Small hybrid heteroaromatics: Resourceful biological tools in cancer research. RSC advances, 7(45), 28313-28349.
  • Ackermann, L. (2011). Carboxylate-assisted transition-metal-catalyzed C− H bond functionalizations: mechanism and scope. Chemical reviews, 111(3), 1315-1345. Akita, Y., Inoue, A., Yamamoto, K., Ohta, A., Kurihara, T., & Shimizu, M. (1985). Palladium-catalyzed coupling reaction of chloropyrazines with indole. Heterocycles (Sendai), 23(9), 2327-2333.
  • Aktaş, A., Celepci, D. B., Gök, Y., & Aygün, M. (2018). 2‐Hydroxyethyl‐Substituted Pd‐PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki‐Miyaura Reaction for Aryl Chlorides in Aqueous Media. ChemistrySelect, 3(35), 9974-9980.
  • Arduengo III, A. J., Harlow, R. L., & Kline, M. (1991). A stable crystalline carbene. Journal of the American Chemical Society, 113(1), 361-363.
  • Arduengo III, A. J., Goerlich, J. R., Krafczyk, R., & Marshall, W. J. (1998). 1, 3, 4, 5‐Tetraphenylimidazol‐2‐ylidene: The Realization of Wanzlick's Dream. Angewandte Chemie International Edition, 37(13‐14), 1963-1965.
  • Arıcı, H., Sündü, B., Fırıncı, R., Ertuğrul, E., Özdemir, N., Cetinkaya, B., ... & Günay, M. E. (2021). The synthesis of new PEPPSI-type N-heterocyclic carbene (NHC)-Pd (II) complexes bearing long alkyl chain as precursors for the synthesis of NHC-stabilized Pd (0) nanoparticles and their catalytic applications. Journal of Organometallic Chemistry, 934, 121633.
  • Beaupré, S., & Leclerc, M. (2013). PCDTBT: en route for low cost plastic solar cells. Journal of Materials Chemistry A, 1(37), 11097-11105.
  • Bhardwaj, V., Gumber, D., Abbot, V., Dhiman, S., & Sharma, P. (2015). Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics. Rsc Advances, 5(20), 15233-15266.
  • Borah, D., Saha, B., Sarma, B., & Das, P. (2020). A new PEPPSI type N-heterocyclic carbene palladium (II) complex and its efficiency as a catalyst for Mizoroki-Heck cross-coupling reactions in water. Journal of Chemical Sciences, 132(1), 1-10.
  • Boztepe, C., Künkül, A., & Gürbüz, N. (2020). Hydrogel supported vinylimidazole based PEPPSI-Pd-NHC catalysts: The catalytic activities in Heck and Suzuki-Miyaura coupling reactions. Journal of Molecular Structure, 1209, 127948.
  • Cazin, C.S.J. (2011). N-heterocyclic Carbenes in Transition Metal Catalysis, Springer, New York.
  • Crabtree, R. H. (2006). Some chelating C-donor ligands in hydrogen transfer and related catalysis. Journal of organometallic chemistry, 691(14), 3146-3150.
  • Danopoulos, A. A., Simler, T., & Braunstein, P. (2019). N-heterocyclic carbene complexes of copper, nickel, and cobalt. Chemical reviews, 119(6), 3730-3961.
  • Daşgın, S., Gök, Y., Celepci, D. B., Taslimi, P., Izmirli, M., Aktaş, A., & Gülçin, İ. (2021). Synthesis, characterization, crystal structure and bioactivity properties of the benzimidazole-functionalized PEPPSI type of Pd (II) NHC complexes. Journal of Molecular Structure, 1228, 129442.
  • Deng, P., Liu, L., Ren, S., Li, H., & Zhang, Q. (2012). N-acylation: an effective method for reducing the LUMO energy levels of conjugated polymers containing five-membered lactam units. Chemical Communications, 48(55), 6960-6962.
  • Divya, K .R., Gari, G. L., Teja, G., Yamini, A.P. & Padmavathi, V. (2019). Chem. Biodiver.
  • Eicher, T., Hauptmann, S., & Speicher, A. (2013). The chemistry of heterocycles: structures, reactions, synthesis, and applications. John Wiley & Sons.
  • Erdemir, F., Barut Celepci, D., Aktaş, A., & Gök, Y. (2019). 2‐hydroxyethyl‐substituted (NHC) PdI2 (pyridine)(Pd‐PEPPSI) Complexes: Synthesis, Characterization and the Catalytic Activity in the Sonogashira Cross‐coupling Reaction. ChemistrySelect, 4(19), 5585-5590.
  • Erdoğan, H., Aktaş, A., Gök, Y., & Sarı, Y. (2018). N-Propylphthalimide-substituted bis-(NHC) PdX2 complexes: synthesis, characterization and catalytic activity in direct arylation reactions. Transition Metal Chemistry, 43(1), 31-37.
  • Filimonov, S. N., Liu, W., & Tkatchenko, A. (2017). Molecular seesaw: Intricate dynamics and versatile chemistry of heteroaromatics on metal surfaces. The Journal of Physical Chemistry Letters, 8(6), 1235-1240.
  • Fortman, G. C., & Nolan, S. P. (2011). N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union. Chemical Society Reviews, 40(10), 5151-5169.
  • Glorius, F. (2006). N-heterocyclic carbenes in catalysis—An introduction.
  • Gokanapalli, A., Motakatla, V. K. R., & Peddiahgari, V. G. R. (2020). Benzimidazole bearing Pd–PEPPSI complexes catalyzed direct C2‐arylation/heteroarylation of N‐substituted benzimidazoles. Applied Organometallic Chemistry, 34(10), e5869.
  • Gök, Y., Aktaş, A., Erdoğan, H., & Sarı, Y. (2018). New 4-vinylbenzyl-substituted bis (NHC)-Pd (II) complexes: Synthesis, characterization and the catalytic activity in the direct arylation reaction. Inorganica Chimica Acta, 471, 735-740.
  • Hagui, W., Doucet, H., & Soulé, J. F. (2019). Application of palladium-catalyzed C (sp2)–H bond arylation to the synthesis of polycyclic (hetero) aromatics. Chem, 5(8), 2006-2078.
  • Herrmann, W. A. (2002). N‐heterocyclic carbenes: a new concept in organometallic catalysis. Angewandte Chemie International Edition, 41(8), 1290-1309.
  • Herrmann, W. A., Schütz, J., Frey, G. D., & Herdtweck, E. (2006). N-heterocyclic carbenes: synthesis, structures, and electronic ligand properties. Organometallics, 25(10), 2437-2448.
  • Hopkinson, M. N., Richter, C., Schedler, M., & Glorius, F. (2014). An overview of N-heterocyclic carbenes. Nature, 510(7506), 485-496.
  • İmik, F., Yaşar, S., & Özdemir, İ. (2019). Synthesis and investigation of catalytic activity of phenylene–And biphenylene bridged bimetallic Palladium-PEPPSI complexes. Journal of Organometallic Chemistry, 896, 162-167.
  • Jiao, L. Y., Yin, X. M., Liu, S., Zhang, Z., Sun, M., & Ma, X. X. (2020). 1, 2, 3-Triazol-5-ylidene bearing a pyridine auxiliary based bidentate PEPPSI type palladium (II) complex: Synthesis, structure, and application in the direct arylation of pyridine N-oxide. Catalysis Communications, 135, 105889.
  • Kim, D., Choi, G., Kim, W., Kim, D., Kang, Y. K., & Hong, S. H. (2021). The site-selectivity and mechanism of Pd-catalyzed C (sp 2)–H arylation of simple arenes. Chemical science, 12(1), 363-373.
  • Lvov, A. G., Khusniyarov, M. M., & Shirinian, V. Z. (2018). Azole-based diarylethenes as the next step towards advanced photochromic materials. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, 36, 1-23.
  • Mao, S., Shi, X., Soulé, J. F., & Doucet, H. (2020). Direct Arylations of Heteroarenes with Benzenesulfonyl Chlorides Using Pd/C Catalyst. European Journal of Organic Chemistry, 2020(1), 91-97.
  • Mishra, K., & Lee, Y. R. (2019). Highly synergistic effect of bifunctional Ru-rGO catalyst for enhanced hydrogenative-reductive benzylation of N-heteroaromatics. Journal of Catalysis, 376, 77-86.
  • O’Brien, C. J., & Kantchev, E. A. B. (2006). C. 35 Valente, N. Hadei, GA Chass, A. Lough, AC Hopkinson and M. G. Organ. Chem. Eur. J, 12, 4743.
  • Organ, M. G., Chass, G. A., Fang, D. C., Hopkinson, A. C., & Valente, C. (2008). Pd-NHC (PEPPSI) complexes: Synthetic utility and computational studies into their reactivity. Synthesis, 2008(17), 2776-2797.
  • Öfele, K. (1968). 1, 3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer Übergangsmetall-carben-komplex. Journal of Organometallic Chemistry, 12(3), P42-P43.
  • Price, G. A., Hassan, A., Chandrasoma, N., Bogdan, A. R., Djuric, S. W., & Organ, M. G. (2017). Pd‐PEPPSI‐IPent‐SiO2: A Supported Catalyst for Challenging Negishi Coupling Reactions in Flow. Angewandte Chemie, 129(43), 13532-13535.
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There are 53 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Articles
Authors

Semra Daşgın 0000-0003-1346-0375

Yetkin Gök 0000-0003-3993-7733

Aydın Aktaş 0000-0001-8496-6782

Project Number İUBAP: 2015/10
Early Pub Date September 26, 2022
Publication Date September 30, 2022
Published in Issue Year 2022 Issue: 40

Cite

APA Daşgın, S., Gök, Y., & Aktaş, A. (2022). 4-Vynilbenzil Grubu Taşıyan Benzimidazol Fonksiyonelleştirilmiş PEPPSI tipi Pd(II)NHC Komplekslerinin Dizaynı, Sentezi, Karakterizasyonu ve Doğrudan Arilasyon Reaksiyonundaki Katalitik Aktivitesi. Avrupa Bilim Ve Teknoloji Dergisi(40), 7-14. https://doi.org/10.31590/ejosat.1168351
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