Maegawa Tomohiro, Kitamura Yoshiaki, Sako Satoko, Udzu Takahiro, Sakurai Ai, Tanaka Asami, Kobayashi Yusuke, Endo Koichi, Bora Utpal, Kurita Takanori, Kozaki Atsushi, Monguchi Yasunari, Sajiki Hironao
Laboratory of Medicinal Chemistry, Gifu Pharmaceutical University, Mitahora-higashi, Gifu 502-8585, Japan.
Chemistry. 2007;13(20):5937-43. doi: 10.1002/chem.200601795.
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.
开发了一种由多相Pd/C催化的温和高效的无配体铃木-宫浦偶联反应。芳基溴化物和三氟甲磺酸酯在室温下于水性介质中，在不存在任何添加剂的情况下，与芳基硼酸进行交叉偶联，产率优异。芳基乙烯基硼酸也适用于此偶联反应，并以高产率提供反式二苯乙烯衍生物。在有氧条件下，湿型Pd/C应用于偶联反应时活性没有任何损失，并且Pd/C可重复使用五次，活性没有明显损失。对4-溴硝基苯与苯硼酸反应混合物的滤液进行电感耦合等离子体质谱分析表明，在检测器的检测限内（<1 ppm），钯金属几乎不会浸出到溶液中，因此表明目前的铃木-宫浦反应是通过多相催化进行的。
