An Efficient Protocol for a Pd(OAc)2-Catalyzed Ligand-Free Suzuki Reaction in Toluene

被引:11
作者
Liu Ning [1 ]
Liu Chun [1 ]
Jin Zilin [1 ]
机构
[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Liaoning, Peoples R China
关键词
Suzuki reaction; arylboronic acid; aryl halide; palladium; ligand-free; toluene; CROSS-COUPLING REACTIONS; FREE PALLADIUM CATALYSIS; ROOM-TEMPERATURE; ARYL CHLORIDES; BOND FORMATION; NANOPARTICLES; WATER;
D O I
10.1016/S1872-2067(10)60119-2
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient protocol for a Pd(OAc)(2)-catalyzed ligand-free Suzuki reaction of aryl bromides with arylboronic acids in the presence of K3PO4 center dot 7H(2)O in toluene under mild and aerobic conditions afforded cross-coupling products in good to excellent yields. Under the optimized reaction conditions (i.e., 0.5 mmol ArBr, 0.75 mmol ArB(OH)(2), 1 mol% Pd(OAc)(2), 1.0 mmol K3PO4 center dot 7H(2)O, 2 ml toluene), the Suzuki reaction between 4-nitrobromobenzene and phenylboronic acid afforded a 99% isolated yield in 5 min at 75 degrees C and a TOF of up to 1 188 h(-1).
引用
收藏
页码:1316 / 1320
页数:5
相关论文
共 32 条
[1]   Use of "homeopathic" ligand-free palladium as catalyst for aryl-aryl coupling reactions [J].
Alimardanov, A ;
de Vondervoort, LSV ;
de Vries, AHM ;
de Vries, JG .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1812-1817
[2]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[3]   Organostannoxane-Supported Palladium Nanoparticles. Highly Efficient Catalysts for Suzuki-Coupling Reactions [J].
Chandrasekhar, Vadapalli ;
Narayanan, Ramakirushnan Suriya ;
Thilagar, Pakkirisamy .
ORGANOMETALLICS, 2009, 28 (20) :5883-5888
[4]   Preparation of a cobalt-containing P,N-bidentate ligand ligated palladium complex: Its applications in amination and Suzuki cross-coupling reactions [J].
Chiang, Wen-Yuan ;
Hong, Fung-E .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2009, 694 (9-10) :1473-1481
[5]   Monoligated palladium species as catalysts in cross-coupling reactions [J].
Christmann, U ;
Vilar, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (03) :366-374
[6]   Very Fast Suzuki-Miyaura Reaction Catalyzed by Pd(OAc)2 under Aerobic Conditions at Room Temperature in EGME/H2O [J].
Del Zotto, Alessandro ;
Amoroso, Francesco ;
Baratta, Walter ;
Rigo, Pierluigi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (01) :110-116
[7]   Aerobic ligand-free Suzuki coupling reaction of aryl chlorides catalyzed by in situ generated palladium nanoparticles at room temperature [J].
Han, Wei ;
Liu, Chun ;
Jin, Zilin .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (03) :501-508
[8]   In situ generation of palladium nanoparticles: A simple and highly active protocol for oxygen-promoted ligand-free suzuki coupling reaction of aryl chlorides [J].
Han, Wei ;
Liu, Chun ;
Jin, Zi-Lin .
ORGANIC LETTERS, 2007, 9 (20) :4005-4007
[9]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[10]   Efficient Assembled Pd/C Catalyst Applied in Suzuki Coupling Reactions [J].
Huang Zhongbin ;
Yan Xinhuan ;
Jiang Lingchao ;
Jiang Hong .
CHINESE JOURNAL OF CATALYSIS, 2010, 31 (01) :90-94