An efficient and recoverable palladium organocatalyst for Suzuki reaction in aqueous media

被引:11
作者
Fareghi-Alamdari, Reza [1 ]
Golestanzadeh, Mohsen [1 ,2 ]
Bagheri, Omid [3 ]
机构
[1] Malek Ashtar Univ Technol, Coll Chem & Chem Engn, Tehran 167653454, Iran
[2] Univ Kashan, Dept Organ Chem, Fac Chem, Kashan 8731751167, Iran
[3] Univ Kashan, Dept Inorgan Chem, Fac Chem, Kashan 8731751167, Iran
关键词
cross-coupling reaction; heterogeneous catalyst; organocatalyst; reusable; water media; CROSS-COUPLING REACTIONS; ORGANOBORON COMPOUNDS; MIYAURA REACTION; CARBOCYCLIC CARBENE; ROOM-TEMPERATURE; ARYL CHLORIDES; WATER; COMPLEXES; CATALYSTS; LIGANDS;
D O I
10.1002/aoc.3698
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Meso-tetrakis[4-(methoxycarbonyl)phenyl]porphyrinatopalladium(II) as a palladium organocatalyst was synthesized and then used in aqueous media as a heterogeneous organocatalyst in Suzuki reaction. The prepared organocatalyst was characterized using UV-visible, infrared and NMR spectroscopies. It was found to be an efficient catalyst for Suzuki coupling reaction between phenylboronic acid and a broad range of aryl halides. Mild reaction conditions, water solvent as green media, and easy catalyst separation and reusability are the advantages of the presented method.
引用
收藏
页数:8
相关论文
共 43 条
[1]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[2]  
[Anonymous], 2008, METAL CATALYZED CROS
[3]   Carbon-carbon coupling reactions catalyzed by supported Pd porphyrins [J].
Bagheri, Omid ;
Sadegh, Faranak ;
Moghadam, Majid ;
Tangestaninejad, Shahram ;
Mirkhani, Valiollah ;
Mohammadpoor-Baltork, Iraj ;
Safiri, Mahsa .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (05) :337-346
[4]   Palladium(II) complex with a potential N4-type Schiff-base ligand as highly efficient catalyst for Suzuki-Miyaura reactions in aqueous media [J].
Banik, Biplab ;
Tairai, Archana ;
Shahnaz, Nasifa ;
Das, Pankaj .
TETRAHEDRON LETTERS, 2012, 53 (42) :5627-5630
[5]   Generation of an aromatic amide-derived phosphane (Aphos) library by self-assisted molecular editing and applications of Aphos in room-temperature Suzuki-Miyaura reactions [J].
Dai, Wei-Min ;
Li, Yannian ;
Zhang, Ye ;
Yue, Congyong ;
Wu, Jinlong .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) :5538-5554
[6]   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
[7]   Immobilized Pd(0) nanoparticles on phosphine-functionalized graphene as a highly active catalyst for Heck, Suzuki and N-arylation reactions [J].
Fareghi-Alamdari, Reza ;
Haqiqi, Mohsen G. ;
Zekri, Negar .
NEW JOURNAL OF CHEMISTRY, 2016, 40 (02) :1287-1296
[8]   Preparation and application of SBA-15-supported palladium catalyst for Suzuki reaction in supercritical carbon dioxide [J].
Feng, Xiujuan ;
Yan, Mei ;
Zhang, Tao ;
Liu, Ying ;
Bao, Ming .
GREEN CHEMISTRY, 2010, 12 (10) :1758-1766
[9]  
Fleckenstein CA, 2007, GREEN CHEM, V9, P1287, DOI 10.1039/b711965h
[10]   Palladium Catalysts with Sulfonate-Functionalized-NHC Ligands for Suzuki-Miyaura Cross-Coupling Reactions in Water [J].
Godoy, Fernando ;
Segarra, Candela ;
Poyatos, Macarena ;
Peris, Eduardo .
ORGANOMETALLICS, 2011, 30 (04) :684-688