Solvent-free Sonogashira coupling reaction via high speed ball milling
Solvent-free Sonogashira coupling reaction via high speed ball milling
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DOI：
10.1039/b915669k
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发表时间：
2009-01-01
期刊：
影响因子：
9.8
通讯作者：
Mack, James
中科院分区：
文献类型：
--
作者：
Fulmer, Dennis A.;Shearouse, William C.;Mack, James
在此，我们报告了利用高速球磨的无溶剂 Sonogashira 反应。各种对位取代的芳基卤化物与三甲基甲硅烷基乙炔或苯乙炔进行 Sonogashira 偶联。我们观察到碘和溴取代的芳族化合物成功地进行了 Sonogashira 偶联。然而，氯和氟取代的芳基化合物不具有反应性。在没有碘化铜的情况下进行偶联反应导致产率低。或者，如果用铜瓶中的铜球代替碘化铜进行反应，则可以高产率观察到偶联产物。这展示了关于在球磨化学反应中使用小瓶和球材料作为催化剂的第一份报告。
Herein, we report on the solvent-free Sonogashira reaction utilizing high speed ball milling. Sonogashira coupling of a variety of para substituted aryl halides were performed with trimethylsilylacetylene or phenylacetylene. We observed that iodo and bromo substituted aromatics successfully undergo Sonogashira coupling. However, chloro and fluoro substituted aryl compounds were unreactive. Conducting the coupling reaction in the absence of copper iodide led to low yields. Alternately, if the reaction is conducted with a copper ball in a copper vial in lieu of copper iodide, the coupling product is observed in high yields. This demonstrates the first report on the use of the vial and ball material as a catalyst in a ball milled chemical reaction.