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Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold

Yıl 2024, Cilt: 20 Sayı: 3, 40 - 46, 30.09.2024
https://doi.org/10.18466/cbayarfbe.1513027

Öz

In catalytic transformations, electronic s-donor properties are signifcantly affected by the presence of the heterocyclic skeleton Among heterocyclic skeletons, imidazole is among the most preferred in catalyst chemistry. In addition, the application of palladium complexes in sp2-sp2 carbon-carbon bond formation reactions has been successful. For this purpose, in the study, palladium complex carrying histamine moiety was systematically prepared to catalyze the Suzuki-Miyaura cross coupling reaction of bromobenzene with arylboronic acids to form biaryls in the presence of NaOH as base. All synthesized compound and palladium complex were fully characterized by Fourier Transform Infrared (FTIR) and 1H- and 13C-NMR spectroscopies. As a result of the investigation of the optimum conditions for the Suzuki-Miyaura cross coupling reaction, was determined that it was 30 minute, 82°C, NaOH as the base, and IPA-H2O as the solvent. The presence of the bulky ditertbutyldicarbonate group, which is connected via the N atoms of the histamine skeleton in the structure, and the binding of Pd metal were determined by blanck test experiments to show that it affects the catalytic activity. As a result of the catalytic experiments, it was determined that the synthesized palladium complex was moderately effective in the Suzuki-Miyaura cross-coupling reaction.

Etik Beyan

There are no ethical issues regarding the publication of this study.

Destekleyen Kurum

Ege üniversitesi BAP birimi

Proje Numarası

22224

Teşekkür

Financial support from Ege University (Project 22224) is gratefully acknowledged.

Kaynakça

  • [1]. Alonso, F, Beletskaya, IP, Yus, M. 2008. Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction. Tetrahedron; 64: 3047.
  • [2]. Knappke, CEI, Jacobi von Wangelin, A. 2011. 35 years of palladium-catalyzed cross-coupling with Grignard reagents: how far have we come?. Chemical Society Reviews; 40: 4948.
  • [3]. Jana, R, Pathak, TP, Sigman, MS. 2011. Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners. Chemical Reviews; 111: 1417.
  • [4]. Nicolaou, KC, Bulger, PG, Sarlah, D. 2005. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angewandte Chemie International Edition; 44: 4442–4489.
  • [5]. Corbet, JP, Mignani, G. 2006. Selected Patented Cross-Coupling Reaction Technologies. Chemical Reviews; 106: 26512710.
  • [6]. Levin, E, Ivry, E, Diesendruck, CE, Lemcoff, NG. 2015. Water in N-Heterocyclic Carbene-Assisted Catalysis. Chemical Reviews; 115: 4607.
  • [7]. Yin, L, Liebscher, J. 2007. Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chemical Reviews; 107: 133–137.
  • [8]. Beletskaya, IP, Alonso, F, Tyurin, V. 2019. The Suzuki-Miyaura reaction after the Nobel prize. Coordination Chemistry Reviews; 385: 137–173.
  • [9]. Torborg, C, Beller, M. 2009. Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries. Advanced Synthesis Catalysis; 351: 3027–3043.
  • [10]. So, CM, Kwong, FY. 2011. Palladium-catalyzed cross-coupling reactions of aryl mesylates. Chemical Society Reviews; 40: 4963.
  • [11]. Grushin, VV, Alper, H. 1994. Transformations of Chioroarenes, Catalyzed by Transition-Metal Complexes. Chemical Reviews; 94: 1047-1062.
  • [12]. Diederich, F, Stang, PJ. uzuki, A. In Metal-Catalyzed Cross-Coupling Reactions, Eds.; Wiley-VCH: Weinheim, Germany, 1998, Chapter 2.
  • [13]. Shen, W. 1997. Palladium catalyzed coupling of aryl chlorides with arylboronic acids. Tetrahedron Letter; 38: 5575-5578.
  • [14]. Miyaura, N, Yanagi, T, Suzuki, A. 2006. The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases. Synthesis Communation; 11: 513-519.
  • [15]. Grasa, GA, Viciu, MS, Huang, J, Zhange, C, Trudell, ML, Nolan, SP. 2002. Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt Systems. Organometallics; 21: 2866.
  • [16]. Nelson, DJ, Nolan, SP. 2013. Quantifying and understanding the electronic properties of N-heterocyclic carbenes. Chemical Society Reviews; 42: 6723.
  • [17]. Mitchell, MB, Wallbank, PJ. 1991. Coupling of heteroaryl chlorides with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium(II) dichloride. Tetrahedron Letter; 32: 2273-2276.
  • [18]. Firooznia, F, Gude, C, Chan, K, Satoh, Y. 1998. Synthesis of 4-substituted phenylalanines by cross-coupling reactions: Extension of the methodology to aryl chlorides. Tetrahedron Letter; 39: 3985-3988.
  • [19]. Bumagin, NA, Bykov. VV. 1997. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media. Tetrahedron; 53: 14437-14450.
  • [20]. Beller, M, Fischer, H, Herrmann, WA, Öfele, K, Brossmer, C. 1995. Angewandte Chemie International Edition; 34: 1848-1849.
  • [21]. Movassagh, B, Hajizadeh, F, Mohammadi, E. 2018. Polystyrene-supported Pd(II)–N-heterocyclic carbene complex as a heterogeneous and recyclable precatalyst for cross-coupling of acyl chlorides with arylboronic acids. Applied Organometalic Chemistry; 32: e3982.
  • [22]. Benhamou, L, Chardon, E, Lavigne, G, Bellemin-Laponnaz, S, César, V. 2011. Synthetic routes to N-heterocyclic carbene precursors. Chemical Review; 111: 2705-2733.
  • [23]. He, X-X, Li, Y, Ma, B-B, Ke, Z, Liu, F-S. 2016. Sterically encumbered tetraarylimidazolium carbene Pd-PEPPSI complexes: highly efficient direct arylation of imidazoles with aryl bromides under aerobic conditions. Organometallics; 35: 2655-2663.
  • [24]. Winkler, A, Brandhorst, K, Freytag, M, Jones, PG, Tamm, M. 2016. Palladium (II) complexes with anionic N-heterocyclic carbene–borate ligands as catalysts for the amination of aryl halides. Organometallics; 35: 1160-1169.
  • [25]. Tu, T, Sun, Z, Fang, W, Xu, M, Zhou, Y. 2012. Robust acenaphthoimidazolylidene palladium complexes: highly efficient catalysts for suzuki–miyaura couplings with sterically hindered substrates. Organic letters; 14: 4250-4253.
  • [26]. Altenhoff, G, Goddard, R, Lehmann, CW, Glorius, F. 2004. Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis. American Chemical Society; 126: 15195-15201.
  • [27]. Valente, C, Pompeo, M, Sayah, M, Organ, MG. 2014. Carbon–heteroatom coupling using Pd-PEPPSI complexes. Organic Process Research & Development; 18: 180-190.
  • [28]. Organ, MG, Çalimsiz, S, Sayah, M, Hoi, KH, Lough, AJ. 2009. Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls. Angewandte Chemie International Edition; 48: 2383-2387.
  • [29]. Çakır, S, Türkmen, G, Türkmen, H. 2018. Palladium(II) complexes bearing Nalkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity. Applied Organometallic Chemistry; 32: e3969.
  • [30]. Çakır, S, Kavukcu, SB, Karabıyık, H, Rethinam, S, Türkmen, H. 2021. C(acyl)–C(sp2) and C(sp2)–C(sp2) Suzuki–Miyaura cross-coupling reactions using nitrilefunctionalized NHC palladium complexes. RSC advances; 11: 37684-37699.
Yıl 2024, Cilt: 20 Sayı: 3, 40 - 46, 30.09.2024
https://doi.org/10.18466/cbayarfbe.1513027

Öz

Proje Numarası

22224

Kaynakça

  • [1]. Alonso, F, Beletskaya, IP, Yus, M. 2008. Non-conventional methodologies for transition-metal catalysed carbon–carbon coupling: a critical overview. Part 2: The Suzuki reaction. Tetrahedron; 64: 3047.
  • [2]. Knappke, CEI, Jacobi von Wangelin, A. 2011. 35 years of palladium-catalyzed cross-coupling with Grignard reagents: how far have we come?. Chemical Society Reviews; 40: 4948.
  • [3]. Jana, R, Pathak, TP, Sigman, MS. 2011. Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners. Chemical Reviews; 111: 1417.
  • [4]. Nicolaou, KC, Bulger, PG, Sarlah, D. 2005. Palladium-Catalyzed Cross-Coupling Reactions in Total Synthesis. Angewandte Chemie International Edition; 44: 4442–4489.
  • [5]. Corbet, JP, Mignani, G. 2006. Selected Patented Cross-Coupling Reaction Technologies. Chemical Reviews; 106: 26512710.
  • [6]. Levin, E, Ivry, E, Diesendruck, CE, Lemcoff, NG. 2015. Water in N-Heterocyclic Carbene-Assisted Catalysis. Chemical Reviews; 115: 4607.
  • [7]. Yin, L, Liebscher, J. 2007. Carbon−Carbon Coupling Reactions Catalyzed by Heterogeneous Palladium Catalysts. Chemical Reviews; 107: 133–137.
  • [8]. Beletskaya, IP, Alonso, F, Tyurin, V. 2019. The Suzuki-Miyaura reaction after the Nobel prize. Coordination Chemistry Reviews; 385: 137–173.
  • [9]. Torborg, C, Beller, M. 2009. Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries. Advanced Synthesis Catalysis; 351: 3027–3043.
  • [10]. So, CM, Kwong, FY. 2011. Palladium-catalyzed cross-coupling reactions of aryl mesylates. Chemical Society Reviews; 40: 4963.
  • [11]. Grushin, VV, Alper, H. 1994. Transformations of Chioroarenes, Catalyzed by Transition-Metal Complexes. Chemical Reviews; 94: 1047-1062.
  • [12]. Diederich, F, Stang, PJ. uzuki, A. In Metal-Catalyzed Cross-Coupling Reactions, Eds.; Wiley-VCH: Weinheim, Germany, 1998, Chapter 2.
  • [13]. Shen, W. 1997. Palladium catalyzed coupling of aryl chlorides with arylboronic acids. Tetrahedron Letter; 38: 5575-5578.
  • [14]. Miyaura, N, Yanagi, T, Suzuki, A. 2006. The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases. Synthesis Communation; 11: 513-519.
  • [15]. Grasa, GA, Viciu, MS, Huang, J, Zhange, C, Trudell, ML, Nolan, SP. 2002. Suzuki−Miyaura Cross-Coupling Reactions Mediated by Palladium/Imidazolium Salt Systems. Organometallics; 21: 2866.
  • [16]. Nelson, DJ, Nolan, SP. 2013. Quantifying and understanding the electronic properties of N-heterocyclic carbenes. Chemical Society Reviews; 42: 6723.
  • [17]. Mitchell, MB, Wallbank, PJ. 1991. Coupling of heteroaryl chlorides with arylboronic acids in the presence of [1,4-bis-(diphenylphosphine)butane]palladium(II) dichloride. Tetrahedron Letter; 32: 2273-2276.
  • [18]. Firooznia, F, Gude, C, Chan, K, Satoh, Y. 1998. Synthesis of 4-substituted phenylalanines by cross-coupling reactions: Extension of the methodology to aryl chlorides. Tetrahedron Letter; 39: 3985-3988.
  • [19]. Bumagin, NA, Bykov. VV. 1997. Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media. Tetrahedron; 53: 14437-14450.
  • [20]. Beller, M, Fischer, H, Herrmann, WA, Öfele, K, Brossmer, C. 1995. Angewandte Chemie International Edition; 34: 1848-1849.
  • [21]. Movassagh, B, Hajizadeh, F, Mohammadi, E. 2018. Polystyrene-supported Pd(II)–N-heterocyclic carbene complex as a heterogeneous and recyclable precatalyst for cross-coupling of acyl chlorides with arylboronic acids. Applied Organometalic Chemistry; 32: e3982.
  • [22]. Benhamou, L, Chardon, E, Lavigne, G, Bellemin-Laponnaz, S, César, V. 2011. Synthetic routes to N-heterocyclic carbene precursors. Chemical Review; 111: 2705-2733.
  • [23]. He, X-X, Li, Y, Ma, B-B, Ke, Z, Liu, F-S. 2016. Sterically encumbered tetraarylimidazolium carbene Pd-PEPPSI complexes: highly efficient direct arylation of imidazoles with aryl bromides under aerobic conditions. Organometallics; 35: 2655-2663.
  • [24]. Winkler, A, Brandhorst, K, Freytag, M, Jones, PG, Tamm, M. 2016. Palladium (II) complexes with anionic N-heterocyclic carbene–borate ligands as catalysts for the amination of aryl halides. Organometallics; 35: 1160-1169.
  • [25]. Tu, T, Sun, Z, Fang, W, Xu, M, Zhou, Y. 2012. Robust acenaphthoimidazolylidene palladium complexes: highly efficient catalysts for suzuki–miyaura couplings with sterically hindered substrates. Organic letters; 14: 4250-4253.
  • [26]. Altenhoff, G, Goddard, R, Lehmann, CW, Glorius, F. 2004. Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis. American Chemical Society; 126: 15195-15201.
  • [27]. Valente, C, Pompeo, M, Sayah, M, Organ, MG. 2014. Carbon–heteroatom coupling using Pd-PEPPSI complexes. Organic Process Research & Development; 18: 180-190.
  • [28]. Organ, MG, Çalimsiz, S, Sayah, M, Hoi, KH, Lough, AJ. 2009. Pd-PEPPSI-IPent: an active, sterically demanding cross-coupling catalyst and its application in the synthesis of tetra-ortho-substituted biaryls. Angewandte Chemie International Edition; 48: 2383-2387.
  • [29]. Çakır, S, Türkmen, G, Türkmen, H. 2018. Palladium(II) complexes bearing Nalkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity. Applied Organometallic Chemistry; 32: e3969.
  • [30]. Çakır, S, Kavukcu, SB, Karabıyık, H, Rethinam, S, Türkmen, H. 2021. C(acyl)–C(sp2) and C(sp2)–C(sp2) Suzuki–Miyaura cross-coupling reactions using nitrilefunctionalized NHC palladium complexes. RSC advances; 11: 37684-37699.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kataliz ve Reaksiyon Mekanizmaları
Bölüm Makaleler
Yazarlar

Sinem Çakır 0000-0003-1387-9643

Hayati Türkmen 0000-0001-7411-2652

Proje Numarası 22224
Yayımlanma Tarihi 30 Eylül 2024
Gönderilme Tarihi 9 Temmuz 2024
Kabul Tarihi 29 Ağustos 2024
Yayımlandığı Sayı Yıl 2024 Cilt: 20 Sayı: 3

Kaynak Göster

APA Çakır, S., & Türkmen, H. (2024). Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, 20(3), 40-46. https://doi.org/10.18466/cbayarfbe.1513027
AMA Çakır S, Türkmen H. Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold. CBUJOS. Eylül 2024;20(3):40-46. doi:10.18466/cbayarfbe.1513027
Chicago Çakır, Sinem, ve Hayati Türkmen. “Synthesis and Catalytic Properties of Palladium Complex With Histamine Scaffold”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20, sy. 3 (Eylül 2024): 40-46. https://doi.org/10.18466/cbayarfbe.1513027.
EndNote Çakır S, Türkmen H (01 Eylül 2024) Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20 3 40–46.
IEEE S. Çakır ve H. Türkmen, “Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold”, CBUJOS, c. 20, sy. 3, ss. 40–46, 2024, doi: 10.18466/cbayarfbe.1513027.
ISNAD Çakır, Sinem - Türkmen, Hayati. “Synthesis and Catalytic Properties of Palladium Complex With Histamine Scaffold”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi 20/3 (Eylül 2024), 40-46. https://doi.org/10.18466/cbayarfbe.1513027.
JAMA Çakır S, Türkmen H. Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold. CBUJOS. 2024;20:40–46.
MLA Çakır, Sinem ve Hayati Türkmen. “Synthesis and Catalytic Properties of Palladium Complex With Histamine Scaffold”. Celal Bayar Üniversitesi Fen Bilimleri Dergisi, c. 20, sy. 3, 2024, ss. 40-46, doi:10.18466/cbayarfbe.1513027.
Vancouver Çakır S, Türkmen H. Synthesis and Catalytic Properties of Palladium Complex with Histamine Scaffold. CBUJOS. 2024;20(3):40-6.