Yeni Kitosan-Glioksal Küre Destekli Pd II Katalizörü: Sentezi, Karakterizasyonu ve Suzuki Kenetlenme Reaksiyonlarindaki Uygulaması

Yıl 2016, Cilt: 44 Sayı: 3, 307 - 315, 01.09.2016

Talat Baran

Öz

B u çalışmada, Suzuki çapraz kenetlenme tepkimeleri için yeni bir kitosan boncuk destekli Pd II katalizörü hazırlandı ve yapısı FTIR, XRD, TGA, SEM/EDAX ve ICP-OES analizleri ile karakterize edildi. Katalizörün, katalitik ve tekrar kullanılabilirlik performansları mikrodalga ısıtma altında ve çözücüsüz ortamda biaril bileşiklerinin sentezinde araştırıldı. Katalizör basit ve hızlı bir mikrodalga ısıtma yöntemi ileiyi dönüşüm tepkime verimleri ve yüksek TON ve TOF değerleri sağladı. Ayrıca optimum koşullar altında tekrar kullanılabilirlik testleri katalizörün beş çevrime kadar kullanılabileceğini gösterdi

Anahtar Kelimeler

Kenetleme tepkimeleri, biaril, tekrar kullanılabilirlik, kitosan, Schiff bazı

New Chitosan-Glyoxal Beads Supported Pd II Catalyst: Synthesis, Characterization and Application in Suzuki Coupling Reactions

Öz

In this paper, a new chitosan bead supported Pd II catalyst was prepared and its structure was characteri- zed with FTIR, XRD, TGA, SEM/EDAX and ICP-OES analyses for Suzuki coupling reactions. The catalytic and recyclable performances of the catalyst were explored in the synthesis of biaryl compounds under microwave heating and free solvent media. The catalyst provided good conversion reaction yields and high TON and TOF values with a simple and quick microwave heating procedure. In addition, the recycle tests indicated that the catalyst could be used for up to seven runs under optimum reaction conditions.

Anahtar Kelimeler

Coupling reactions, biaryl, reusability, chitosan, Schiff base

Kaynakça

• A.-R. Hajipour, F. Rafiee, Dimeric ortho-palladated complex of 2,3-dimethoxybenzaldehyde oxime catalyzed Suzuki-Miyaura cross-coupling reaction under microwave irradiation, J. Iran. Chem. Soc., 12 (2015) 1177-1181.
• B.C.E. Makhubela, A. Jardine, G.S. Smith, Pd nanosized particles supported on chitosan and deoxy-6-amino chitosan as recyclable catalysts for Suzuki–Miyaura and Heck cross-coupling reactions, Appl. Catal. A-Gen., 393 (2011) 231-241.
• P. Cotugno, M. Casiello, A. Nacci, P. Mastrorilli, M.M. Dell’Anna, A. Monopoli, Suzuki coupling of iodo and bromoarenes catalyzed by chitosan-supported Pd- nanoparticles in ionic liquids, J. Organomet. Chem., (2014) 1-5.
• Y. Chang, Y. Lv, F. Lu, F. Zha, Z. Lei, Efficient allylic oxidation of cyclohexene with oxygen catalyzed by chloromethylated polystyrene supported tridentate Schiff-base complexes, J. Mol. Catal. A-Chem., 320 (2010) 56-61.
• P. Puthiaraj, W.-S. Ahn, Highly active palladium nanoparticles immobilized on NH2-MIL-125 as efficient and recyclable catalysts for Suzuki–Miyaura cross coupling reaction, Catal. Commun., 65 (2015) 95.
• X. Wang, P. Hu, F. Xue, Y. Wei, Cellulose-supported N-heterocyclic carbene-palladium catalyst: Synthesis and its applications in the Suzuki cross-coupling reaction, Carbohyd. Polym., 114 (2014) 476-483.
• Y. Xiang, Q. Zhang, J. Si, J. Du, H. Guo, T. Zhang, Characterization and catalytic kinetics studies of N-cetyl-O-sulfate chitosan multinuclear copper complex as an artificial hydrolase, J. Mol. Catal. A-Chem., 322 (2010) 33-38.
• İ. Uslu, H. Çelikkan, O. Atakol, M.L. Aksu, Preparation of PVA/chitosan doped with boron composite fibers and their characterization, Hacettepe J. Biol. & Chem., 36 (2008) 117-122.
• D. de Britto, O.B.G. Assis, A novel method for obtaining a quaternary salt of chitosan, Carbohyd. Polym., 69 (2007) 305-310.
• L.S. Guinesi, É.T.G. Cavalheiro, Influence of some reactional parameters on the substitution degree of biopolymeric Schiff bases prepared from chitosan and salicylaldehyde, Carbohyd. Polym., 65 (2006) 561. TOF st nd rd th th
• Reaction conditions: 1.12 mmol 4-bromoanisole, 1.87 mmol phenyl boronic acid, 3.75 mmol base, 0.025% mol chitosan bead supported Pd(II) catalyst, 50°C, 5 min under MW.