The direct synthesis of symmetrical disulfides and diselenides by metal-organic framework MOF-199 as an efficient heterogenous catalyst

被引：37
作者：
Soleiman-Beigi, Mohammad [1 ]
Yavari, Issa [2 ]
Sadeghizadeh, Fatemeh [1 ]
机构：
[1] Ilam Univ, Conclus Chem Dept, Ilam, Iran
[2] Tarbiat Modares Univ, Chem Dept, Tehran, Iran
来源：
RSC ADVANCES | 2015年 / 5卷 / 106期
关键词：
ONE-POT SYNTHESIS; ARYL HALIDES; S-S; CHEMOSELECTIVE SYNTHESIS; ANTIOXIDANT ACTIVITY; ALKYL; THIOLS; BOND; OXIDATION; CHEMISTRY;
D O I：
10.1039/c5ra16879a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly crystalline porous copper-based metal-organic framework MOF-199 was synthesized, and characterized by several techniques, including XRD, EDX, SEM, and FT-IR. MOF-199 was used as an efficient catalyst for the one-pot and efficient synthesis of organic dichalcogenides from aryl halides (-OTs) and elemental sulfur and selenium in polyethylene glycols (PEGs). A variety of disulfides and diselenides can be obtained in good to excellent yields of up to 98% in a relatively short reaction time.
引用
收藏
页码：87564 / 87570
页数：7
相关论文
共 85 条
[1]   Probing the Lewis acidity and catalytic activity of the metal-organic framework [Cu3(btc)2] (BTC = benzene-1,3,5-tricarboxylate) [J].
Alaerts, Luc ;
Seguin, Etienne ;
Poelman, Hilde ;
Thibault-Starzyk, Frederic ;
Jacobs, Pierre A. ;
De Vos, Dirk E. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (28) :7353-7363
[2]   Copper-catalyzed sulfenylation of pyrroles with disulfides or thiols: directly synthesis of sulfenyl pyrroles [J].
Alves, Diego ;
Lara, Renata G. ;
Contreira, Maria E. ;
Radatz, Catia S. ;
Duarte, Luis F. B. ;
Perin, Gelson .
TETRAHEDRON LETTERS, 2012, 53 (26) :3364-3368
[3]   Synthesis of telluroamino acid derivatives with remarkable GPx like activity [J].
Braga, Antonio L. ;
Alberto, Eduardo E. ;
Soares, Letiere C. ;
Rocha, Joao B. T. ;
Sudati, Jessie H. ;
Roos, Daniel H. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (01) :43-45
[4]   Metal-organic frameworks with high capacity and selectivity for harmful gases [J].
Britt, David ;
Tranchemontagne, David ;
Yaghi, Omar M. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2008, 105 (33) :11623-11627
[5]  
Caldarelli S. A., 2012, J MED CHEM, V55, P461
[6]   TIN RADICAL-ADDITION TO ALKYNYL SULFIDES - REACTIVITY OF THE INTERMEDIATE THIOALKYL-SUBSTITUTED BETA-(TRIBUTYLSTANNYL)VINYL RADICALS [J].
CAPELLA, L ;
MONTEVECCHI, PC ;
NANNI, D .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3368-3374
[7]   A route to high surface area, porosity and inclusion of large molecules in crystals [J].
Chae, HK ;
Siberio-Pérez, DY ;
Kim, J ;
Go, Y ;
Eddaoudi, M ;
Matzger, AJ ;
O'Keeffe, M ;
Yaghi, OM .
NATURE, 2004, 427 (6974) :523-527
[8]   Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al2O3. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides [J].
Chatterjee, Tanmay ;
Ranu, Brindaban C. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7145-7153
[9]   Oxidation of thiols with molecular oxygen catalyzed by cobalt(II) phthalocyanines in ionic liquid [J].
Chauhan, SMS ;
Kumar, A ;
Srinivas, KA .
CHEMICAL COMMUNICATIONS, 2003, (18) :2348-2349
[10]   Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C-S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study [J].
Chen, Hsing-Ying ;
Peng, Wei-Te ;
Lee, Ying-Hsien ;
Chang, Yu-Lun ;
Chen, Yen-Jen ;
Lai, Yi-Chun ;
Jheng, Nai-Yuan ;
Chen, Hsuan-Ying .
ORGANOMETALLICS, 2013, 32 (19) :5514-5522
123456789