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Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions

Year 2023, Volume: 19 Issue: 3, 211 - 218, 30.09.2023

Mehmet Günaltay Hülya Avcı Özbek Funda Demirhan

https://doi.org/10.18466/cbayarfbe.1261392

Abstract

We describe here the first results of catalytic performance of in situ prepared [Pd(O2CCH3)2] / 1,3-bis(ferrocenylmethy)imidazolinium chloride involving a saturated imidazole ring were successfully employed to Suzuki cross-coupling reactions of different aryl bromides (bromobenzene, 2-bromobenzonitrile, 2-bromotoluene, p-bromobenzaldehyde, p-bromoacetophenone, p-bromoanisole, p-bromotoluene and p-bromobenzotrifluoride) with phenylboronic acid under the optimum conditions. Optimum conditions were choosed, as 24 h, 80 oC, K2CO3 as base, dioxane as solvent, 1,3-bis(ferrocenylmethy)imidazolinium chloride as auxiliary ligand. Under these optimum conditions, 2- bromobenzonitrile, p-bromoacetophenone and p- bromobenzaldehyde react with phenyl boronic acid in moderate yields 57%, 50%, and 46% respectively. Catalytic experiments showed that [Pd(O2CCH3)2] / 1,3-bis(ferrocenylmethy)imidazolinium chloride catalytic system was moderately effficent in the Suzuki cross coupling reaction of aryl bromides in dioxane.

Keywords

Ferrocene 1 3-bis(ferrocenylmethy)imidazolinium salt Palladium Suzuki

Supporting Institution

Manisa Celal Bayar University Scientific Research Projects Coordination Unit

Project Number

2015-168

Thanks

This study was supported by Manisa Celal Bayar University Scientific Research Projects Coordination Unit. Project Number: 2015-168

References

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  • [2]. Troiano, R, Costabile, C, Grisi, F. 2022. Alternating Ring-Opening Metathesis Polymerization Promoted by Ruthenium Catalysts Bearing Unsymmetrical NHC Ligands. Catalysts; 13: 34.
  • [3]. Jayaraj, A, Raveedran, AV, Latha, AT, Priyadarshini, D, Ayya Swamy PC. 2023. Coordination Versatility of NHC-metal Topologies in Asymmetric Catalysis: Synthetic Insights and Recent Trends. Coordination Chemistry Reviews. 478:214922.
  • [4]. Ye, Y, Liu Z, Wang, Y, Zhang, Y, Yin, F, He Q, Peng J, Tan K, Shen, Y. 2022. N-Indole-substituted N-heterocyclic carbene palladium precatalysts: Synthesis, characterization and catalytic cross-couplings. Tetrahedron Letters. 107:154125.
  • [5]. Nair, PP, Jayaraj, A, Ayya Swamy PC. 2022. Recent Advances in Benzimidazole Based NHC-Metal Complex Catalysed Cross-Coupling Reactions. ChemistrySelect. 7:e202103517.
  • [6]. Anju, PJ, Neetha, M, Anilkumar, G. 2022. Recent Advances on N-Heterocyclic Carbene-Palladium catalyzed Heck Reaction ChemistrySelect. 7:e202103564.
  • [7]. Bildstein, B, Malaun, M, Kopacka, H, Ongania, K, Wurst, K. 1998. Imidazoline-2-ylidene metal complexes with pendant ferrocenyl substituents. Journal of Organometallic Chemistry. 552:45–61.
  • [8]. Bildstein, B, Malaun, M, Kopacka, H, Ongania, K, Wurst, K. 1999. N-Heterocyclic carbenes with N-ferrocenyl-N′-methyl-substitution: synthesis, reactivity, structure and electrochemistry. Journal of Organometallic Chemistry. 572:177–187.
  • [9]. Bildstein, B, Malaun, M, Kopacka, H, Wurst, K, Mitterböck, M, Ongania, KH, Opromolla, G, Zanello, 1999. P. N,N′-Diferrocenyl-N-Heterocyclic carbenes and their derivatives. Organometallics.18:4325-4336.
  • [10]. Siemeling, U. 2012. Singlet carbenes derived from ferrocene and closely related sandwich complex. European Journal of Inorganic Chemistry. 3523- 3536.
  • [11]. Broggini, D, Togni, A. 2002. Synthesis and structure of an enantiomerically pure C2 symmetric ferrocenyl carbene. Helvatica Chimica Acta. 85: 2518-2522.
  • [12]. Seo, H, Kim, BY, Lee, JH, Park, HJ, Son, SU, Chung, YK. 2003. Synthesis of chiral ferrocenyl imidazolium salts and their rhodium(I) and iridium(I) complexes. Organometallics. 22: 4783-4791.
  • [13]. Gisching, S, Togni, A. 2005. Pd II complexes of tridentate PCP N-heterocyclic carbene ligands: structural aspects and application in asymmetric hydruamination of cyano olefins. European Journal of Inorganic Chemistry. 4745-4754.
  • [14]. Willms, H, Frank, W, Ganter, C. 2008. Hybrid ligands with N-Heterocyclic carbene and chiral phosphaferrocene components. Chemistry-A European Journal. 14: 2719-2729.
  • [15]. Bertogg, A, Camponovo, F, Togni, A. 2004. N-Ferrocenyl-Substituted Planar-Charial N-Heterocyclic Carbenes and Their Pd II Complexes. European Journal of Inorganic Chemistry. 691.
  • [16]. Siemeling, U, Färber, C, Bruhn, C, Fürmeier, S, Schulz, T, Kurlemann, M, Tripp, S. 2010. Group 10 Metal Complexes of a Ferrocene-Based N-Heterocyclic Carbene: Syntheses, Structures and Catalytic Applications. European Journal of Inorganic Chemistry. 1413–1422.
  • [17]. Soni, A, Sharma, C, Negi, L, Joshi, RK. 2023. NHC-Pd (II) full pincer catalyzed Mizoroki-Heck Type Cross-Coupling of Vinyl Chloride and Alkenes: Synthesis of Novel Ferrocenylated Conjugated Dienes. Journal of Organometallic Chemistry. 983: 122550.
  • [18]. Pore, DM, Gaikwad, DS, Patil, JD. 2013. Ferrocene-tagged N-heterocyclic carbene-Pd complex for Suzuki–Miyaura coupling. Monatsh Chemie. 144:1355–1361.
  • [19]. Kale, D, Rashinkar, G, Kumbhar, A, Salunkhe, R. 2017. Facile Suzuki-Miyaura cross coupling using ferrocene tethered N-heterocyclic carbene-Pd complex anchored on cellulose. Reactive and Functional Polymers. 116:9-16.
  • [20]. Gaikwad, V, Kurane, R, Jadhav, J, Salunkhe, R, Rashinkar, G. 2013. A viable synthesis of ferrocene tethered NHC–Pd complex via supported ionic liquid phase catalyst and its Suzuki coupling activity. Applied Catalysis A: General. 451:243–250.
  • [21]. Khanapure, S, Pore, D, Jagadale, M, Patil, V, Rashinka, G. 2021. Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N‑Heterocyclic Carbene‑Palladium Complex. Catalysis Letters. 151:2237–2249.
  • [22]. Shi, JC, Yang, PY, Tong, Q, Wu, Y, Peng, Y. 2006. Highly efficient and stable palladium/imidazolium salt-phosphine catalysts for Suzuki–Miyaura cross-coupling of aryl bromides. Journal of Molecular Catalysis A: Chemical 259:7–10.
  • [23]. Shi, JC, Yang, PY, Tong, Q, Jia, L. 2008. Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands Dalton Transactions. 938–945.
  • [24]. Yu, HW, Shi JC, Zhang, H, Yang, PY, Wang, XP, Jin, ZL. 2006. Unsymmetric-1,3-disubstituted imidazolium salt for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl bromides. Journal of Molecular Catalysis A: Chemical. 250:15–19.
  • [25]. Dallas, A, Kuhtz, H, Farrell, A, Quilty, B, Nolan, K. 2007. Versatile reagents: ferrocenyl azolium compounds as auxiliary ligands for the Heck reaction and potential antifungal agents. Tetrahedron Letters. 48:1017–1021.
  • [26]. Musaoğlu, D, Avcı Özbek, H, Demirhan, F. 2023. Heck coupling reactions of aryl halides catalyzed by saturated ferrocenylmethylimidazolinium salts/palladium. Journal of the Iranian Chemical Society. 20:637–643.
  • [27]. Avcı Özbek, H, Sözen Aktaş, P, Daran JC, Oskay, M, Demirhan, F, Çetinkaya.B. 2014. Synthesis, structure, electrochemical and antimicrobial properties of N,N'-bis(ferrocenylmethyl)imidazolinium salts. Inorganica Chimica Acta. 42:435–442.
  • [28]. Huang, W, Guo, J, Xiao, Y, Zhu, M, Zou, G, Tang, J. 2005. Palladium–benzimidazolium salt catalyst systems for Suzuki coupling: development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acid. Tetrahedron. 61:9783–9790.
  • [29]. Liu, C, Zhang, Y, Liu, N, Qiu, J. 2012. A simple and efficient approach for the palladium-catalyzed ligand-free Suzuki reaction in water. Green Chemistry. 14:2999-3003.
  • [30]. Srinivas, K, Srinivas, P, Prathima, PS, Balaswamy, K, Sridhar, B, Rao, MM. 2012. Catalysis Science & Technology. 2:1180–1187.

Year 2023, Volume: 19 Issue: 3, 211 - 218, 30.09.2023

Mehmet Günaltay Hülya Avcı Özbek Funda Demirhan

https://doi.org/10.18466/cbayarfbe.1261392

Abstract

Project Number

2015-168

References

  • [1]. Angoy, M, Jiménez MV, Lahoz FJ, Vispe, E, Pérez-Torrente JJ. 2022. Polymerization of phenylacetylene catalyzed by rhodium(I) complexes with N-functionalized N-heterocyclic carbene ligands. Polymer Chemistry; 13:1411-1421.
  • [2]. Troiano, R, Costabile, C, Grisi, F. 2022. Alternating Ring-Opening Metathesis Polymerization Promoted by Ruthenium Catalysts Bearing Unsymmetrical NHC Ligands. Catalysts; 13: 34.
  • [3]. Jayaraj, A, Raveedran, AV, Latha, AT, Priyadarshini, D, Ayya Swamy PC. 2023. Coordination Versatility of NHC-metal Topologies in Asymmetric Catalysis: Synthetic Insights and Recent Trends. Coordination Chemistry Reviews. 478:214922.
  • [4]. Ye, Y, Liu Z, Wang, Y, Zhang, Y, Yin, F, He Q, Peng J, Tan K, Shen, Y. 2022. N-Indole-substituted N-heterocyclic carbene palladium precatalysts: Synthesis, characterization and catalytic cross-couplings. Tetrahedron Letters. 107:154125.
  • [5]. Nair, PP, Jayaraj, A, Ayya Swamy PC. 2022. Recent Advances in Benzimidazole Based NHC-Metal Complex Catalysed Cross-Coupling Reactions. ChemistrySelect. 7:e202103517.
  • [6]. Anju, PJ, Neetha, M, Anilkumar, G. 2022. Recent Advances on N-Heterocyclic Carbene-Palladium catalyzed Heck Reaction ChemistrySelect. 7:e202103564.
  • [7]. Bildstein, B, Malaun, M, Kopacka, H, Ongania, K, Wurst, K. 1998. Imidazoline-2-ylidene metal complexes with pendant ferrocenyl substituents. Journal of Organometallic Chemistry. 552:45–61.
  • [8]. Bildstein, B, Malaun, M, Kopacka, H, Ongania, K, Wurst, K. 1999. N-Heterocyclic carbenes with N-ferrocenyl-N′-methyl-substitution: synthesis, reactivity, structure and electrochemistry. Journal of Organometallic Chemistry. 572:177–187.
  • [9]. Bildstein, B, Malaun, M, Kopacka, H, Wurst, K, Mitterböck, M, Ongania, KH, Opromolla, G, Zanello, 1999. P. N,N′-Diferrocenyl-N-Heterocyclic carbenes and their derivatives. Organometallics.18:4325-4336.
  • [10]. Siemeling, U. 2012. Singlet carbenes derived from ferrocene and closely related sandwich complex. European Journal of Inorganic Chemistry. 3523- 3536.
  • [11]. Broggini, D, Togni, A. 2002. Synthesis and structure of an enantiomerically pure C2 symmetric ferrocenyl carbene. Helvatica Chimica Acta. 85: 2518-2522.
  • [12]. Seo, H, Kim, BY, Lee, JH, Park, HJ, Son, SU, Chung, YK. 2003. Synthesis of chiral ferrocenyl imidazolium salts and their rhodium(I) and iridium(I) complexes. Organometallics. 22: 4783-4791.
  • [13]. Gisching, S, Togni, A. 2005. Pd II complexes of tridentate PCP N-heterocyclic carbene ligands: structural aspects and application in asymmetric hydruamination of cyano olefins. European Journal of Inorganic Chemistry. 4745-4754.
  • [14]. Willms, H, Frank, W, Ganter, C. 2008. Hybrid ligands with N-Heterocyclic carbene and chiral phosphaferrocene components. Chemistry-A European Journal. 14: 2719-2729.
  • [15]. Bertogg, A, Camponovo, F, Togni, A. 2004. N-Ferrocenyl-Substituted Planar-Charial N-Heterocyclic Carbenes and Their Pd II Complexes. European Journal of Inorganic Chemistry. 691.
  • [16]. Siemeling, U, Färber, C, Bruhn, C, Fürmeier, S, Schulz, T, Kurlemann, M, Tripp, S. 2010. Group 10 Metal Complexes of a Ferrocene-Based N-Heterocyclic Carbene: Syntheses, Structures and Catalytic Applications. European Journal of Inorganic Chemistry. 1413–1422.
  • [17]. Soni, A, Sharma, C, Negi, L, Joshi, RK. 2023. NHC-Pd (II) full pincer catalyzed Mizoroki-Heck Type Cross-Coupling of Vinyl Chloride and Alkenes: Synthesis of Novel Ferrocenylated Conjugated Dienes. Journal of Organometallic Chemistry. 983: 122550.
  • [18]. Pore, DM, Gaikwad, DS, Patil, JD. 2013. Ferrocene-tagged N-heterocyclic carbene-Pd complex for Suzuki–Miyaura coupling. Monatsh Chemie. 144:1355–1361.
  • [19]. Kale, D, Rashinkar, G, Kumbhar, A, Salunkhe, R. 2017. Facile Suzuki-Miyaura cross coupling using ferrocene tethered N-heterocyclic carbene-Pd complex anchored on cellulose. Reactive and Functional Polymers. 116:9-16.
  • [20]. Gaikwad, V, Kurane, R, Jadhav, J, Salunkhe, R, Rashinkar, G. 2013. A viable synthesis of ferrocene tethered NHC–Pd complex via supported ionic liquid phase catalyst and its Suzuki coupling activity. Applied Catalysis A: General. 451:243–250.
  • [21]. Khanapure, S, Pore, D, Jagadale, M, Patil, V, Rashinka, G. 2021. Sustainable Synthesis of Biaryls Using Silica Supported Ferrocene Appended N‑Heterocyclic Carbene‑Palladium Complex. Catalysis Letters. 151:2237–2249.
  • [22]. Shi, JC, Yang, PY, Tong, Q, Wu, Y, Peng, Y. 2006. Highly efficient and stable palladium/imidazolium salt-phosphine catalysts for Suzuki–Miyaura cross-coupling of aryl bromides. Journal of Molecular Catalysis A: Chemical 259:7–10.
  • [23]. Shi, JC, Yang, PY, Tong, Q, Jia, L. 2008. Palladium-catalyzed aminations of aryl halides with phosphine-functionalized imidazolium ligands Dalton Transactions. 938–945.
  • [24]. Yu, HW, Shi JC, Zhang, H, Yang, PY, Wang, XP, Jin, ZL. 2006. Unsymmetric-1,3-disubstituted imidazolium salt for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl bromides. Journal of Molecular Catalysis A: Chemical. 250:15–19.
  • [25]. Dallas, A, Kuhtz, H, Farrell, A, Quilty, B, Nolan, K. 2007. Versatile reagents: ferrocenyl azolium compounds as auxiliary ligands for the Heck reaction and potential antifungal agents. Tetrahedron Letters. 48:1017–1021.
  • [26]. Musaoğlu, D, Avcı Özbek, H, Demirhan, F. 2023. Heck coupling reactions of aryl halides catalyzed by saturated ferrocenylmethylimidazolinium salts/palladium. Journal of the Iranian Chemical Society. 20:637–643.
  • [27]. Avcı Özbek, H, Sözen Aktaş, P, Daran JC, Oskay, M, Demirhan, F, Çetinkaya.B. 2014. Synthesis, structure, electrochemical and antimicrobial properties of N,N'-bis(ferrocenylmethyl)imidazolinium salts. Inorganica Chimica Acta. 42:435–442.
  • [28]. Huang, W, Guo, J, Xiao, Y, Zhu, M, Zou, G, Tang, J. 2005. Palladium–benzimidazolium salt catalyst systems for Suzuki coupling: development of a practical and highly active palladium catalyst system for coupling of aromatic halides with arylboronic acid. Tetrahedron. 61:9783–9790.
  • [29]. Liu, C, Zhang, Y, Liu, N, Qiu, J. 2012. A simple and efficient approach for the palladium-catalyzed ligand-free Suzuki reaction in water. Green Chemistry. 14:2999-3003.
  • [30]. Srinivas, K, Srinivas, P, Prathima, PS, Balaswamy, K, Sridhar, B, Rao, MM. 2012. Catalysis Science & Technology. 2:1180–1187.
There are 30 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Articles
Authors

Mehmet Günaltay 0009-0001-9604-3982

Hülya Avcı Özbek 0000-0003-1508-2558

Funda Demirhan 0000-0001-9428-9607

Project Number 2015-168
Publication Date September 30, 2023
Published in Issue Year 2023 Volume: 19 Issue: 3

Cite

APA Günaltay, M., Avcı Özbek, H., & Demirhan, F. (2023). Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions. Celal Bayar University Journal of Science, 19(3), 211-218. https://doi.org/10.18466/cbayarfbe.1261392
AMA Günaltay M, Avcı Özbek H, Demirhan F. Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions. CBUJOS. September 2023;19(3):211-218. doi:10.18466/cbayarfbe.1261392
Chicago Günaltay, Mehmet, Hülya Avcı Özbek, and Funda Demirhan. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science 19, no. 3 (September 2023): 211-18. https://doi.org/10.18466/cbayarfbe.1261392.
EndNote Günaltay M, Avcı Özbek H, Demirhan F (September 1, 2023) Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions. Celal Bayar University Journal of Science 19 3 211–218.
IEEE M. Günaltay, H. Avcı Özbek, and F. Demirhan, “Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions”, CBUJOS, vol. 19, no. 3, pp. 211–218, 2023, doi: 10.18466/cbayarfbe.1261392.
ISNAD Günaltay, Mehmet et al. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science 19/3 (September 2023), 211-218. https://doi.org/10.18466/cbayarfbe.1261392.
JAMA Günaltay M, Avcı Özbek H, Demirhan F. Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions. CBUJOS. 2023;19:211–218.
MLA Günaltay, Mehmet et al. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science, vol. 19, no. 3, 2023, pp. 211-8, doi:10.18466/cbayarfbe.1261392.
Vancouver Günaltay M, Avcı Özbek H, Demirhan F. Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions. CBUJOS. 2023;19(3):211-8.
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