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Efficient Iron-Catalyzed Kumada Cross-Coupling Reactions Utilizing Flow Technology under Low Catalyst Loadings
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2016-04-19 , DOI: 10.1002/ejoc.201600275 Frederic G. Buono , Yongda Zhang , Zhulin Tan , Andrew Brusoe , Bing-Shiou Yang , Jon C. Lorenz , Riccardo Giovannini , Jinhua J. Song , Nathan K. Yee , Chris H. Senanayake
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2016-04-19 , DOI: 10.1002/ejoc.201600275 Frederic G. Buono , Yongda Zhang , Zhulin Tan , Andrew Brusoe , Bing-Shiou Yang , Jon C. Lorenz , Riccardo Giovannini , Jinhua J. Song , Nathan K. Yee , Chris H. Senanayake
An efficient continuous flow iron-catalyzed Kumada cross-coupling was developed for the coupling of 2-chloropyrazine and various aryl Grignard reagents in presence of low catalyst loadings (0.5 mol-%). Compared to batch mode, the continuous flow approach overcomes the exothermicity which enabled longer catalyst lifetime, facilitated scale-up and significantly improved the yield. To the best of our knowledge, this is the first example of flow iron-catalyzed Kumada cross-coupling reactions which addresses scale dependence issues which often plague Kumada reactions carried out in the traditional batch mode.
中文翻译:
在低催化剂负载下利用流动技术进行高效的铁催化 Kumada 交叉偶联反应
开发了一种高效的连续流动铁催化 Kumada 交叉偶联,用于在低催化剂负载(0.5 mol%)存在下偶联 2-氯吡嗪和各种芳基格氏试剂。与间歇模式相比,连续流动方法克服了放热问题,从而延长了催化剂寿命,促进了放大并显着提高了产率。据我们所知,这是流动铁催化的熊田交叉偶联反应的第一个例子,它解决了规模依赖性问题,这些问题经常困扰以传统间歇模式进行的熊田反应。
更新日期:2016-04-19
中文翻译:
在低催化剂负载下利用流动技术进行高效的铁催化 Kumada 交叉偶联反应
开发了一种高效的连续流动铁催化 Kumada 交叉偶联,用于在低催化剂负载(0.5 mol%)存在下偶联 2-氯吡嗪和各种芳基格氏试剂。与间歇模式相比,连续流动方法克服了放热问题,从而延长了催化剂寿命,促进了放大并显着提高了产率。据我们所知,这是流动铁催化的熊田交叉偶联反应的第一个例子,它解决了规模依赖性问题,这些问题经常困扰以传统间歇模式进行的熊田反应。