A new chitosan Schiff base supported Pd(II) complex for microwave-assisted synthesis of biaryls compounds

被引:69
作者
Baran, Talat [1 ]
机构
[1] Aksaray Univ, Fac Sci & Letters, Dept Chem, TR-68100 Aksaray, Aksaray, Turkey
关键词
Biaryls; Schiff base; Reusability; TOF; Chitosan; Pd(II) catalyst; CROSS-COUPLING REACTION; SUZUKI-MIYAURA REACTIONS; HIGHLY EFFICIENT; PALLADIUM CATALYST; CU(II); CHLORIDES; HALIDES; WATER;
D O I
10.1016/j.molstruc.2017.03.122
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
In this study, a new heterogeneous palladium (II) catalyst that contains O-carboxymethyl chitosan Schiff base has been designed for Suzuki coupling reactions. The chemical structures of the synthesized catalyst were characterized with the FTIR, TG/DTG, ICP-OES, SEM/EDAX, H-1 NMR, C-13 NMR, GC/MS, XRD, and magnetic moment techniques. The reusability and catalytic behavior of heterogeneous catalyst was tested towards Suzuki reactions. As a result of the tests, excellent selectivity was obtained, and by-products of homo coupling were not seen in the spectra. The biaryls products were identified on a GC/MS. In addition, it was determined in the reusability tests that the catalysts could be used several times (seven runs). More importantly, with very low catalyst loading (6 x 10(-3) mol %) in very short reaction time (5 min), chitosan Schiff base supported Pd(II) complex gave high TON and TOF values. These findings showed that Schiff base supported Pd(II) catalyst is suitable for Suzuki cross coupling reactions. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:535 / 541
页数:7
相关论文
共 34 条
[1]
Oxime-derived palladacycles as source of palladium nanoparticles [J].
Alonso, Diego A. ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (08) :2891-2902
[2]
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
[3]
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
[4]
Highly efficient Suzuki cross-coupling reaction of biomaterial supported catalyst derived from glyoxal and chitosan [J].
Baran, Talat ;
Mentes, Ayfer .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 803 :30-38
[5]
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
[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]
Studies on N-methylene phosphonic chitosan/poly(vinyl alcohol) composite proton-exchange membrane [J].
Binsu, V. V. ;
Nagarale, R. K. ;
Shahi, Vinod K. ;
Ghosh, P. K. .
REACTIVE & FUNCTIONAL POLYMERS, 2006, 66 (12) :1619-1629
[8]
Suzuki coupling of iodo and bromoarenes catalyzed by chitosan-supported Pd-nanoparticles in ionic liquids [J].
Cotugno, Pietro ;
Casiello, Michele ;
Nacci, Angelo ;
Mastrorilli, Piero ;
Dell'Anna, Maria Michela ;
Monopoli, Antonio .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 752 :1-5
[9]
Schiff base-derived homogeneous and heterogeneous palladium catalysts for the Suzuki-Miyaura reaction [J].
Das, Pankaj ;
Linert, Wolfgang .
COORDINATION CHEMISTRY REVIEWS, 2016, 311 :1-23
[10]
A novel method for obtaining a quaternary salt of chitosan [J].
de Britto, Douglas ;
Assis, Odilio B. G. .
CARBOHYDRATE POLYMERS, 2007, 69 (02) :305-310