A mild and versatile method for palladium-catalyzed cross-coupling of aryl halides in water and surfactants

被引:123
作者
Arcadi, A [1 ]
Cerichelli, G [1 ]
Chiarini, M [1 ]
Correa, M [1 ]
Zorzan, D [1 ]
机构
[1] Univ Aquila, Dipartimento Chim Ingn Chim & Mat, I-67010 Laquila, Italy
关键词
cross-coupling; palladium; surfactants;
D O I
10.1002/ejoc.200300356
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Various aqueous surfactants proved to be excellent media for carrying out palladium-catalyzed Suzuki-Miyaura cross-coupling reactions under mild conditions. The dehalogenation side reaction, which is usually a drawback with the aqueous protocol, was not observed. The concentration of the surfactant in water played a pivotal role for the reaction outcome. Smooth cross-coupling of iodoanisole and a variety of aryl bromides, including electron-rich derivatives, with aryl boronic acids occurred at room temperature in high yields either with [Pd(PPh3)(4)] or Pd/C as catalyst. The water-surfactant Pd/C system combines high activity under ambient conditions (air), easy separation and recyclability. Palladium acetate was found to be effective in cross-coupling of the less reactive aryl chlorides at 100 degreesC. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码:4080 / 4086
页数:7
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