Rapid and amenable Suzuki coupling reaction in water using microwave and conventional heating

被引:219
作者
Leadbeater, NE [1 ]
Marco, M [1 ]
机构
[1] Kings Coll London, Dept Chem, London WC2R 2LS, England
关键词
D O I
10.1021/jo0264022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
It is possible to prepare biaryls in good yield very rapidy (5-10 min) on small (1 mmol) and larger (10-20 mmol) scales from aryl halides and phenylboronic acid using water as a solvent and palladium acetate as catalyst. The reaction can be performed equally well using microwave and conventional heating, showing that using these conditions probably no nonthermal microwave effects are associated with the impressive speed of the reaction.
引用
收藏
页码:888 / 892
页数:5
相关论文
共 39 条
[1]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[2]   Highly efficient palladium-catalyzed boronic acid coupling reactions in water: Scope and limitations [J].
Badone, D ;
Baroni, M ;
Cardamone, R ;
Ielmini, A ;
Guzzi, U .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7170-7173
[3]   Microwave-assisted aqueous Suzuki cross-coupling reactions [J].
Blettner, CG ;
König, WA ;
Stenzel, W ;
Schotten, T .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3885-3890
[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]   Water soluble phosphines - Part XV. Syntheses of multiply functionalized and chiral phosphine ligands by Pd-catalyzed P-C and C-C coupling reactions [J].
Brauer, DJ ;
Hingst, M ;
Kottsieper, KW ;
Liek, C ;
Nickel, T ;
Tepper, M ;
Stelzer, O ;
Sheldrick, WS .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) :14-26
[7]   Ligandless palladium catalyzed reactions of arylboronic acids and sodium tetraphenylborate with aryl halides in aqueous media [J].
Bumagin, NA ;
Bykov, VV .
TETRAHEDRON, 1997, 53 (42) :14437-14450
[8]   HIGH YIELDS OF UNSYMMETRICAL BIARYLS VIA CROSS-COUPLING OF ARYLBORONIC ACIDS WITH HALOARENES USING A MODIFIED SUZUKI-BELETSKAYA PROCEDURE [J].
CAMPI, EM ;
JACKSON, WR ;
MARCUCCIO, SM ;
NAESLUND, CGM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (20) :2395-2395
[9]  
Cornils B., 2006, Aqueous -Phase Organometallic Catalysis: Concepts and Applications
[10]   Suzuki cross-coupling of arylboronic acids mediated by a hydrosoluble Pd(0)/TPPTS catalyst [J].
Dupuis, C ;
Adiey, K ;
Charruault, L ;
Michelet, V ;
Savignac, M ;
Genêt, JP .
TETRAHEDRON LETTERS, 2001, 42 (37) :6523-6526