钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应
收稿日期: 2014-07-12
修回日期: 2014-08-17
网络出版日期: 2014-09-09
基金资助
国家基础科学人才培养基金(No.J1103303)和福州大学科研启动基金(No.XRC-1305)资助项目.
Pd-Complex Catalyzed Suzuki Cross-Coupling Reaction of Brominated Salicylaldehyde with Pyridylboronic Acid
Received date: 2014-07-12
Revised date: 2014-08-17
Online published: 2014-09-09
Supported by
Project supported by the National Natural Science Fundation of China (No. J1103303) and the Research Fund of Fuzhou University (No. XRC-1305).
通过研究不同种类钯催化剂[Pd(dppf)2Cl2, Pd(OAc)2, Pd(PPh3)4]、碱(Na2CO3, NaHCO3, K2CO3, K3PO4, Cs2CO3, CsF)、溶剂(DME/H2O, DMF/H2O, Dioxane/H2O)及温度(70, 80, 100 ℃)对5-溴-3-叔丁基水杨醛与吡啶-4-硼酸制备5-(4-吡啶)-3-叔丁基水杨醛化合物的Suzuki偶联反应的影响, 开发出一种高效催化吸或供电子基取代的芳基硼酸与吸电子基取代的溴代芳烃的偶联反应的方法, 该反应在Pd(PPh3)4, K2CO3, Dioxane/H2O (V:V=4:1)、80 ℃的条件下产率达到97%, 且具有分离简单、重现性好的特征; 但对供电子基取代的溴代芳烃参与的反应催化效果一般.
关键词： Suzuki偶联反应; 吡啶硼酸; 溴代芳烃; 催化机理
王碧玉 , 倪沛钟 , 范吉理 , 郑辉东 , 赵素英 , 白正帅 . 钯催化溴代水杨醛与吡啶硼酸的Suzuki交叉偶联反应[J]. 有机化学, 2014 , 34(12) : 2471 -2477 . DOI: 10.6023/cjoc201407024
The synthesis of 3-tert-butyl-2-hydroxy-5-(pyridin-4-yl)benzaldehyde by Suzuki cross coupling reaction of 5-bromo-3-tert-butyl-2-hydroxybenzaldehyde with pyridin-4-ylboronic acid was studied by using different catalysts [Pd(dppf)2Cl2, Pd(OAc)2 and Pd(PPh3)4], bases (Na2CO3, NaHCO3, K2CO3, K3PO4, Cs2CO3 and CsF) and solvents (DME/H2O, DMF/H2O and dioxane/H2O) under different temperature of 70, 80 and 100 ℃. A compatible method was developed for the coupling reaction of arylboronic acids (having electron donating or withdrawing group) with aryl bromides (having electron withdrawing group). Under the condition of Pd(PPh3)4, K2CO3, dioxane/H2O (V:V=4:1), 80 ℃, the yield is excellent (97%) and the product separation is easy. The compatibility for aryl bromides with electron donating group is moderate.
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