Efficient Iron-Catalyzed Kumada Cross-Coupling Reactions Utilizing Flow Technology under Low Catalyst Loadings

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• 作者：Frederic G. Buono ; Yongda Zhang ; Zhulin Tan ; Andrew Brusoe ; Bing-Shiou Yang ; Jon C. Lorenz ; Riccardo Giovannini ; Jinhua J. Song ; Nathan K. Yee and Chris H. Senanayake
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 2016
• 年：2016
• 卷：2016
• 期：15
• 页码：2599-2602
• 全文大小：702K
• ISSN：1099-0690

文摘

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.