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

Yıl 2023, Cilt: 19 Sayı: 3, 211 - 218, 30.09.2023
https://doi.org/10.18466/cbayarfbe.1261392

Öz

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.

Destekleyen Kurum

Manisa Celal Bayar University Scientific Research Projects Coordination Unit

Proje Numarası

2015-168

Teşekkür

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

Kaynakça

  • [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.
Yıl 2023, Cilt: 19 Sayı: 3, 211 - 218, 30.09.2023
https://doi.org/10.18466/cbayarfbe.1261392

Öz

Proje Numarası

2015-168

Kaynakça

  • [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.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Makaleler
Yazarlar

Mehmet Günaltay 0009-0001-9604-3982

Hülya Avcı Özbek 0000-0003-1508-2558

Funda Demirhan 0000-0001-9428-9607

Proje Numarası 2015-168
Yayımlanma Tarihi 30 Eylül 2023
Yayımlandığı Sayı Yıl 2023 Cilt: 19 Sayı: 3

Kaynak Göster

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. Eylül 2023;19(3):211-218. doi:10.18466/cbayarfbe.1261392
Chicago Günaltay, Mehmet, Hülya Avcı Özbek, ve Funda Demirhan. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science 19, sy. 3 (Eylül 2023): 211-18. https://doi.org/10.18466/cbayarfbe.1261392.
EndNote Günaltay M, Avcı Özbek H, Demirhan F (01 Eylül 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, ve F. Demirhan, “Palladium/1,3-bis(ferrocenylmethy)imidazolinium chloride catalyst for Suzuki cross-coupling reactions”, CBUJOS, c. 19, sy. 3, ss. 211–218, 2023, doi: 10.18466/cbayarfbe.1261392.
ISNAD Günaltay, Mehmet vd. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science 19/3 (Eylül 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 vd. “Palladium/1,3-bis(ferrocenylmethy)imidazolinium Chloride Catalyst for Suzuki Cross-Coupling Reactions”. Celal Bayar University Journal of Science, c. 19, sy. 3, 2023, ss. 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.