Efficient protocol for the phosphine-free Suzuki-Miyaura reaction catalyzed by palladium on carbon at room temperature

被引:81
作者
Zhang, GL [1 ]
机构
[1] Zhejiang Univ, Coll Pharmaceut Sci, Dept Med Chem, Hangzhou 310031, Peoples R China
来源
SYNTHESIS-STUTTGART | 2005年 / 04期
关键词
Suzuki-Miyaura coupling; palladium; catalysis; heterogeneous;
D O I
10.1055/s-2004-837298
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and efficient protocol for the phosphine-free Suzuki-Miyaura coupling reaction of aryl bromides with arylboronic acids has been developed which utilizes the commercially available 10% Pd/C (3.5 mol% Pd) in ethanol-water (1:1) and Na2CO3 at room temperature. The reaction is convenient, environmentally benign and generates excellent yields of the coupled products (94-100%). The catalyst can be recycled using simple filtration and washing sequences without significant decrease in the yield of coupling product up to the fourth run.
引用
收藏
页码:537 / 542
页数:6
相关论文
共 47 条
[1]   Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
ORGANIC LETTERS, 2000, 2 (13) :1823-1826
[2]   Orthopalladated and -platinated bulky triarylphosphite complexes: Synthesis, reactivity and application as high-activity catalysts for Suzuki and Stille coupling reactions [J].
Bedford, RB ;
Hazlewood, SL ;
Limmert, ME ;
Albisson, DA ;
Draper, SM ;
Scully, PN ;
Coles, SJ ;
Hursthouse, MB .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3216-3227
[3]   Highly active catalysts for the Suzuki coupling of aryl chlorides [J].
Bedford, RB ;
Cazin, CSJ .
CHEMICAL COMMUNICATIONS, 2001, (17) :1540-1541
[4]  
Botella L, 2002, ANGEW CHEM INT EDIT, V41, P179, DOI 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO
[5]  
2-O
[6]   SYNTHESIS AND FUNGISTATIC ACTIVITY OF SOME 3-HYDROXYBIPHENYL DERIVATIVES [J].
BRADSHER, CK ;
BROWN, FC ;
PORTER, HK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (09) :2357-2362
[7]   Cross-coupling reactions of arylsilanols with substituted aryl halides [J].
Denmark, SE ;
Ober, MH .
ORGANIC LETTERS, 2003, 5 (08) :1357-1360
[8]   Preparation of enantiopure 4-arylmandelic acids via a Pd/C catalysed Suzuki coupling of enantiopure 4-bromomandelic acid [J].
Dyer, UC ;
Shapland, PD ;
Tiffin, PD .
TETRAHEDRON LETTERS, 2001, 42 (09) :1765-1767
[9]   Multikilogram-scale synthesis at a biphenyl carboxylic acid derivative using a Pd/C-mediated Suzuki coupling approach [J].
Ennis, DS ;
McManus, J ;
Wood-Kaczmar, W ;
Richardson, J ;
Smith, GE ;
Carstairs, A .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (04) :248-252
[10]   Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids [J].
Feuerstein, M ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2001, 42 (38) :6667-6670