First microwave-accelerated hiyama coupling of aryl- and vinylsiloxane derivatives: Clean cross-coupling of aryl chlorides within minutes

被引:51
作者
Clarke, ML [1 ]
机构
[1] Univ St Andrews, Sch Chem, St Andrews, Fife, Scotland
关键词
cross-coupling; homogeneous catalysis; microwave heating; palladium; phosphane ligands;
D O I
10.1002/adsc.200404196
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The first microwave-accelerated Hiyama cross-coupling reactions are reported. The reactions of aryl bromides and activated aryl chlorides with PhSi(OMe)(3) [or C2H3Si(OMe)(3)] are complete within minutes using a modified catalyst system that can be prepared from commercially available reagents in situ. The microwave-accelerated reactions proceed under relatively mild conditions (110-115degreesC).
引用
收藏
页码:303 / 307
页数:5
相关论文
共 30 条
[1]   NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES [J].
BABA, S ;
NEGISHI, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) :6729-6731
[2]   Rapid microwave-promoted Suzuki cross coupling reaction in water [J].
Bai, L ;
Wang, JX ;
Zhang, YM .
GREEN CHEMISTRY, 2003, 5 (05) :615-617
[3]   High-activity catalysts for Suzuki coupling and amination reactions with deactivated aryl chloride substrates: Importance of the palladium source [J].
Bedford, RB ;
Cazin, CSJ ;
Coles, SJ ;
Gelbrich, T ;
Horton, PN ;
Hursthouse, MB ;
Light, ME .
ORGANOMETALLICS, 2003, 22 (05) :987-999
[4]   Platinum complexes of tertiary amine functionalised phosphines [J].
Clarke, ML ;
Slawin, AMZ ;
Woollins, JD .
POLYHEDRON, 2003, 22 (01) :19-26
[5]   Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides [J].
Clarke, ML ;
Cole-Hamilton, DJ ;
Woollins, JD .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (19) :2721-2723
[6]  
CLARKE ML, 2003, J CHEM SOC DA, P4393
[7]   The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides:: Use of commercially available Pd(P(t-BU)3)2 as a catalyst [J].
Dai, CY ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) :2719-2724
[8]  
Denmark SE, 2003, ALDRICHIM ACTA, V36, P75
[9]   Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system [J].
Fürstner, A ;
Seidel, G .
ORGANIC LETTERS, 2002, 4 (04) :541-543
[10]   Cross-coupling reactions of aryl chlorides with organochlorosilanes: Highly effective methods for arylation or alkenylation of aryl chlorides [J].
Gouda, K ;
Hagiwara, E ;
Hatanaka, Y ;
Hiyama, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7232-7233