Highly efficient Suzuki cross-coupling reaction of biomaterial supported catalyst derived from glyoxal and chitosan

被引:53
作者
Baran, Talat [1 ]
Mentes, Ayfer [1 ]
机构
[1] Aksaray Univ, Fac Sci & Letters, Dept Chem, TR-68100 Aksaray, Turkey
关键词
Heterogeneous catalyst; C-C coupling; O-Carboxymethyl chitosan; TG/DTG; Glyoxal; BASE MODIFIED CHITOSAN; CARBOXYMETHYL CHITOSAN; SCHIFF-BASE; THERMAL-DECOMPOSITION; PD(II) COMPLEXES; CU(II); DEACETYLATION; CO(II); CHITIN;
D O I
10.1016/j.jorganchem.2015.12.011
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学];
摘要
In this study a new chitosan based water soluble Schiff base was produced through carboxymethylation of chitosan and its Pd(II) complex were synthesized and characterized by FTIR, H-1 NMR, C-13 CP-MAS NMR, TG/DTG, SEM/EDAX, XRD, ICP-OES, UV-Vis, magnetic moment measurements, molar conductivity measurements. The catalytic activity of the complex was tested in Suzuki coupling reactions for synthesis of biaryls containing various substrates. The identifications of the biarlys were performed by H-1 NMR and GC-MS. The catalytic activity tests revealed that high selectivity was achieved with a small addition of the catalyst. Moreover by-product formation was not observed in the spectra of H-1 NMR and GC-MS. Mercury poisoning and leaching test confirmed that the catalyst has heterogeneous character. The reusability tests showed that the catalyst did not lose its activity after six runs. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:30 / 38
页数:9
相关论文
共 36 条
[1]
Preparation, characterization and pH-metric measurements of 4-hydroxysalicylidenechitosan Schiff-base complexes of Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Ru(III), Rh(III), Pd(II) and Au(III) [J].
Anan, Neveen A. ;
Hassan, Shawky M. ;
Saad, Eman M. ;
Butler, Ian S. ;
Mostafa, Sahar I. .
CARBOHYDRATE RESEARCH, 2011, 346 (06) :775-793
[2]
Synthesis, spectroscopic and catalytic studies of Cu(II), Co(II) and Ni(II) complexes immobilized on Schiff base modified chitosan [J].
Antony, R. ;
Manickam, S. Theodore David ;
Saravanan, K. ;
Karuppasamy, K. ;
Balakumar, S. .
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1050 :53-60
[3]
Synthesis, spectrochemical characterisation and catalytic activity of transition metal complexes derived from Schiff base modified chitosan [J].
Antony, R. ;
David, S. Theodore ;
Saravanan, K. ;
Karuppasamy, K. ;
Balakumar, S. .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 103 :423-430
[4]
Carboxymethyl chitosan Schiff base supported heterogeneous palladium(II) catalysts for Suzuki cross-coupling reaction [J].
Baran, Talat ;
Aciksoz, Eda ;
Mentes, Ayfer .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2015, 407 :47-52
[5]
Cu(II) and Pd(II) complexes of water soluble O-carboxymethyl chitosan Schiff bases: Synthesis, characterization [J].
Baran, Talat ;
Mentes, Ayfer .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2015, 79 :542-554
[6]
Synthesis and characterization of water soluble O-carboxymethyl chitosan Schiff bases and Cu(II) complexes [J].
Baran, Talat ;
Mentes, Ayfer ;
Arslan, Hulya .
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2015, 72 :94-103
[7]
Effect of deacetylation time on the preparation, properties and swelling behavior of chitosan films [J].
Baskar, D. ;
Kumar, T. S. Sampath .
CARBOHYDRATE POLYMERS, 2009, 78 (04) :767-772
[8]
Triphenylphosphine chalcogenides as efficient ligands for room temperature palladium(II)-catalyzed Suzuki-Miyaura reaction [J].
Das, Pankaj ;
Bora, Utpal ;
Tairai, Archana ;
Sharma, Chandan .
TETRAHEDRON LETTERS, 2010, 51 (11) :1479-1482
[9]
Spectroscopy analysis of chitosan-glibenclamide hydrogels [J].
Delgadillo-Armendariz, Nancy-Liliana ;
Rangel-Vazquez, Norma-Aurea ;
Garcia-Castanon, Alejandra-Ibeth .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2014, 120 :524-528
[10]
Synthesis of the ketimine of chitosan and 4,6-diacetylresorcinol, and study of the catalase-like activity of its copper chelate [J].
Demetgul, Cahit .
CARBOHYDRATE POLYMERS, 2012, 89 (02) :354-361