Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media
Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media
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DOI：
10.1002/chem.200601795
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发表时间：
2007-01-01
影响因子：
4.3
通讯作者：
Sajiki, Hironao
中科院分区：
文献类型：
--
作者：
Maegawa, Tomohiro;Kitamura, Yoshiaki;Sajiki, Hironao
开发了一种由非均相 Pd/C 催化的温和高效的无配体 Suzuki-Miyaura 偶联反应。芳基溴和三氟甲磺酸酯在室温下在水介质中不存在任何添加剂的情况下以优异的产率与芳基硼酸发生交叉偶联。芳基乙烯基硼酸也适用于该偶联反应并以高产率提供反式二苯乙烯衍生物。湿式Pd/C在偶联反应中的应用在有氧条件下实现了，没有任何活性损失，并且Pd/C的重复使用可以进行第五次运行而没有明显的活性损失。对 4-溴硝基苯与苯基硼酸的反应混合物的滤液进行电感耦合等离子体 (ICP) 质谱分析表明，在检测器的限制内 (< 1 ppm)，钯金属几乎不会浸出到溶液中，从而表明目前的 Suzuki-Miyaura 反应是通过非均相催化进行的。
A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (< 1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis.