水对苯硼酸参与的偶联反应的促进作用  

Effect of Water on Arylboronic Acid Mediated Cross-Coupling Reaction

作　　者：辛炳炜[1] 

机构地区：[1]德州学院化学系,德州253023

出　　处：《应用化学》2008年第8期895-898,共4页Chinese Journal of Applied Chemistry

基　　金：国家自然科学基金资助项目(20571063)

摘　　要：研究了水对离子液体或聚乙二醇中Pd(OAc)2催化的卤代苯或苯甲酰氯与苯硼酸的Suzuki和Suzuki-Type偶联反应收率的影响。证明当其它条件不变时,水能极大提高在离子液体和PEG中偶联反应的收率,并且对于Suzuki反应和Suzuki-Type反应,水与IL和PEG的最佳质量比不同。对于Suzuki反应,[bmim][PF6]∶H2O的最佳质量比为3∶1(收率为99%),而当离子液体为[bmim][BF4]时,与H2O的最佳比例为3∶3(93%)。当[bmim][PF6]∶H2O和PEG2000∶H2O的质量比分别为3∶2.5和3∶3时,Suzuki-Type反应活性最高,收率可分别达82%和94%。同时还讨论了水促进偶联反应的可能机理。We studied the effect of water on the palladium acetate-catalyzed coupling reaction of aryl boronic acid with aryl bromide or acyl chloride in ionic liquid or PEG, and found that water had a remarkable rate accelerating effect on the Suzuki reaction and Suzuki-Type reaction when other reaction conditions were uniform. The ratio of water to IL or PEG was pivotal to the reaction, and the optimal ratio of water to IL or PEG was different to the Suzuki and Suzuki-Type reactions. When the ratio of [ bmim] [ PF6 ] and water was 3： 1, the best yield of 99% of Suzuki reaction was achieved, while the optimal ratio of [ bmim ] [ BF4 ] to water was 3：3（93% ）. The Suzuki-Type reaction delivered the good yield of 82% in the [ bmim] [ PF6 ]-H2O system when the mass ratio of [ bmim] [ PF6 ] to water was 3：2. 5, while in the PEG-H2O system, the optimal ratio of PEG to water was 3 ： 3 （ yield was 94% ）. The possible mechanism of water influence on the cross-coupling reaction was discussed.

关 键 词：水 离子液体 PEG 苯硼酸 SUZUKI偶联反应 Suzuki—Type偶联反应 

分 类 号：O623.6[理学—有机化学]