Palladium nanoparticles as reusable catalyst for the synthesis of N-aryl sulfonamides under mild reaction conditions

被引:18
作者
Khalaj, Mehdi [1 ]
Ghazanfarpour-Darjani, Majid [1 ]
Olyai, Mohamad Reza Talei Bavil [2 ]
Shamami, Sakineh Faraji [3 ]
机构
[1] Islamic Azad Univ, Buinzahra Branch, Dept Chem, Buinzahra, Iran
[2] Islamic Azad Univ, Fac Sci South Tehran Branch, Dept Chem, Tehran, Iran
[3] Islamic Azad Univ, Karaj Branch, Dept Chem, Karaj, Iran
关键词
Sulfonamide; aryl halide; C-N Cross-coupling; palladium nanoparticles; aryl triflate; SUZUKI COUPLING REACTION; LIGAND-FREE; BORONIC ACIDS; COPPER; ARYLATION; BROMIDES; IODIDES; DERIVATIVES; CHLORIDES; SULFONYL;
D O I
10.1080/17415993.2015.1122010
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient palladium nanoparticles-catalyzed N-arylation of sulfonamides and sulfonyl azides is described. This procedure serves as an active protocol for intermolecular C-N bond formation using Pd(OAc)(2) in PEG-400 under air. Aryl bromides and triflates react at 35 degrees C, while aryl chlorides require heating to 50 degrees C and give the desired products only in low yields. This reaction proceeds smoothly in acceptable yields using low catalyst loading.
引用
收藏
页码:211 / 221
页数:11
相关论文
共 31 条
[1]   Synthesis and in vitro anticancer evaluation of some novel hexahydroquinoline derivatives having a benzenesulfonamide moiety [J].
Al-Said, Mansour S. ;
Ghorab, Mostafa M. ;
Al-Dosari, Mohammed S. ;
Hamed, Mostafa M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) :201-207
[2]   Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].
Astruc, D ;
Lu, F ;
Aranzaes, JR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872
[3]   C-N bond forming cross-coupling reactions: an overview [J].
Bariwal, Jitender ;
Van der Eycken, Erik .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9283-9303
[4]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[5]   Palladium-catalyzed intermolecular coupling of aryl chlorides and sulfonamides under microwave irradiation [J].
Burton, G ;
Cao, P ;
Li, G ;
Rivero, R .
ORGANIC LETTERS, 2003, 5 (23) :4373-4376
[6]  
Cal V, 2006, EUR J ORG CHEM, V2006, P3791, DOI [10.1002/ejoc.200600045, DOI 10.1002/EJOC.200600045]
[7]   Polyethyleneglycol as scaffold and solvent for reusable C-C coupling homogeneous Pd catalysts [J].
Corma, Avelino ;
Garcia, Hermenegildo ;
Leyva, Antonio .
JOURNAL OF CATALYSIS, 2006, 240 (02) :87-99
[8]   BippyPhos: A Single Ligand With Unprecedented Scope in the Buchwald-Hartwig Amination of (Hetero) aryl Chlorides [J].
Crawford, Sarah M. ;
Lavery, Christopher B. ;
Stradiotto, Mark .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (49) :16760-16771
[9]   Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands [J].
Deng, W ;
Liu, L ;
Zhang, C ;
Liu, M ;
Guo, QX .
TETRAHEDRON LETTERS, 2005, 46 (43) :7295-7298
[10]   Mild and efficient CuI catalyzed coupling reactions of amides with bromides [J].
Deng, W ;
Zhang, C ;
Liu, M ;
Zou, Y ;
Liu, L ;
Guo, QX .
CHINESE JOURNAL OF CHEMISTRY, 2005, 23 (09) :1241-1246