Highly ordered mesoporous La(III)-substituted 5-oxopyrrolidine-2-carboxylic acid (Glp) immobilized on SBA-15 as a very efficient nanocatalyst for green aerobic oxidative coupling of thiols to disulfides

被引:25
作者
Molaei, Somayeh [1 ]
Ghadermazi, Mohammad [1 ]
机构
[1] Univ Kurdistan, Fac Sci, Dept Chem, Sanandaj 6617715175, Iran
关键词
aerobic oxidation; La(III) and nanoporous catalyst; thiols; CATALYST; NANOPARTICLES; SILICA; SULFIDES;
D O I
10.1002/aoc.5328
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Selective aerobic oxidative coupling of thiols that are catalyzed by La(III)-substituted 5-oxopyrrolidine-2-carboxylic acid (Glp) immobilized on SBA-15 (SBA-15@Glp-La; SBA = Santa Barbara amorphous) was studied. Using SBA-15@Glp-La, the complete conversion was achieved at room temperature in the presence of air without producing any over-oxidized yields. SBA-15@Glp-La was prepared by post-grafting technique. 5-Oxopyrrolidine-2-carboxylic acid (Glp) condensation followed by La(III) impregnation caused this La(III)-grafted 5-oxopyrrolidine-2-carboxylic acid (Glp) to immobilize on SBA-15. This SBA-15@Glp-La catalyst shows excellent catalytic activity in the selective aerobic oxidative coupling of thiols. Effects of amount of the catalyst, polarity of the solvent, effects of substrate, and catalyst reusability were investigated. It has been observed that seven repetitive reaction cycles did not cause any appreciable loss in the catalytic activity of this catalyst. The catalyst characterization by scanning electron microscopy, energy-dispersive X-ray spectroscopy, X-ray diffraction, Fourier-transform infrared spectroscopy, thermal gravimetric analysis, transmission electron microscopy, inductively coupled plasma, elemental mapping, and N-2 adsorption-desorption is reported. The procedure developed is heterogeneous and environmentally benign.
引用
收藏
页数:14
相关论文
共 44 条
[1]   Rhenium-catalyzed oxidation of thiols and disulfides with sulfoxides [J].
Arterburn, JB ;
Perry, MC ;
Nelson, SL ;
Dible, BR ;
Holguin, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (39) :9309-9310
[2]   Photocatalytic Chemoselective Aerobic Oxidation of Thiols to Disulfides Catalyzed by Combustion Synthesized Bismuth Tungstate Nanoparticles in Aqueous Media [J].
Bhoi, Yagna Prakash ;
Rout, Durga Prasad ;
Mishra, B. G. .
JOURNAL OF CLUSTER SCIENCE, 2016, 27 (01) :267-284
[3]   Mesoporous Silica Nanoparticles for Active Corrosion Protection [J].
Borisova, Dimitriya ;
Moehwald, Helmuth ;
Shchukin, Dmitry G. .
ACS NANO, 2011, 5 (03) :1939-1946
[4]   Nonviral Cell Labeling and Differentiation Agent for Induced Pluripotent Stem Cells Based on Mesoporous Silica Nanoparticles [J].
Chen, Wei ;
Tsai, Ping-Hsing ;
Hung, Yann ;
Chiou, Shih-Hwa ;
Mou, Chung-Yuan .
ACS NANO, 2013, 7 (10) :8423-8440
[5]   Synthesis and characterization of SBA-polyperoxyacid: An efficient heterogeneous solid peroxyacid catalyst for epoxidation of alkenes [J].
Davarpanah, Jamal ;
Kiasat, Ali Reza .
CATALYSIS COMMUNICATIONS, 2014, 46 :75-80
[6]   Aerobic Oxidation of Thiols Catalyzed by Copper Nanoparticles Supported on Diamond Nanoparticles [J].
Dhakshinamoorthy, Amarajothi ;
Navalon, Sergio ;
Sempere, David ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
CHEMCATCHEM, 2013, 5 (01) :241-246
[7]   Aerobic oxidation of thiols to disulfides using iron metal-organic frameworks as solid redox catalysts [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
CHEMICAL COMMUNICATIONS, 2010, 46 (35) :6476-6478
[8]   Manganese octahedral molecular sieve (OMS-2) catalysts for selective aerobic oxidation of thiols to disulfides [J].
Dharmarathna, Saminda ;
King'ondu, Cecil K. ;
Pahalagedara, Lakshitha ;
Kuo, Chung-Hao ;
Zhang, Yashan ;
Suib, Steven L. .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2014, 147 :124-131
[9]   Aerobic oxidation of thiols to disulfides catalyzed by a manganese(III) Schiff-base complex [J].
Golchoubian, Hamid ;
Hosseinpoor, Farideh .
CATALYSIS COMMUNICATIONS, 2007, 8 (04) :697-700
[10]   Selective and efficient oxidation of sulfides and thiols with benzyltriphenylphosphonium peroxymonosulfate in aprotic solvent [J].
Hajipour, AR ;
Mallakpour, SE ;
Adibi, H .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) :8666-8668