Hydrazine-mediated Reduction of Nitro and Azide Functionalities Catalyzed by Highly Active and Reusable Magnetic Iron Oxide Nanocrystals
Hydrazine-mediated Reduction of Nitro and Azide Functionalities Catalyzed by Highly Active and Reusable Magnetic Iron Oxide Nanocrystals
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DOI：
10.1021/jo400556g
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发表时间：
2013-05-03
影响因子：
3.6
通讯作者：
Kappe, C. Oliver
中科院分区：
文献类型：
--
作者：
Cantillo, David;Moghaddam, Mojtaba Mirhosseini;Kappe, C. Oliver
从廉价易得的铁源原位生成的氧化铁（Fe3O4）纳米晶体以无与伦比的效率催化硝基芳烃还原为苯胺。该程序具有化学选择性，避免使用贵金属，可在轻度回流条件下（65或80摄氏度）或在高温（150摄氏度）下使用密封容器微波加热。利用微波条件，在150℃下，在2-8分钟内以接近定量的产量制备了多种功能化苯胺，该方法也成功地应用于脂肪族硝基化合物和叠氮化物的还原。氧化铁纳米颗粒以胶体形式产生，从而产生适合连续流动处理的均匀溶液。选定的工业上重要的苯胺的例子已经在一个连续的制度下使用该协议制备。
Iron oxide (Fe3O4) nanocrystals generated in situ from an inexpensive and readily available iron source catalyze the reduction of nitroarenes to anilines with unparalleled efficiency. The procedure is chemoselective, avoids the use of precious metals, and can be applied under mild reflux conditions (65 or 80 degrees C) or using sealed vessel microwave heating in an elevated temperature regime (150 degrees C). Utilizing microwave conditions, a variety of functionalized anilines have been prepared in nearly quantitative yields within 2-8 min at 150 degrees C, in a procedure also successfully applied to the reduction of aliphatic nitro compounds and azides. The iron oxide nanoparticles are generated in a colloidal form, resulting in homogeneous solutions suitable for continuous flow processing. Selected examples of anilines of industrial importance have been prepared in a continuous regime using this protocol.