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Palladium Immobilized onto Functionalized Magnetic Nanoparticles as Robust Catalysts for Amination and Room‐Temperature Ullmann Homocoupling of Aryl Halides: A Walk Around the C−F Bond Activation
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-02-23 , DOI: 10.1002/ajoc.201800041 Firouz Matloubi Moghaddam 1 , Raheleh Pourkaveh 1 , Ashkan Karimi 1 , Seyed Ebrahim Ayati 1
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-02-23 , DOI: 10.1002/ajoc.201800041 Firouz Matloubi Moghaddam 1 , Raheleh Pourkaveh 1 , Ashkan Karimi 1 , Seyed Ebrahim Ayati 1
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The first example of a heterogeneous catalytically active system for Buchwald–Hartwig and Ullmann homocoupling of unactivated aryl halides (fluorobenzene) is presented. The novel magnetic heterogeneous palladium catalyst was synthesized by immobilization of palladium ions onto an aminopyridine‐functionalized Fe3O4. The catalyst was fully characterized by FTIR spectroscopy, temperature‐programmed reduction, thermogravimetric analysis, CHN elemental analysis, transmission electron microscopy, field‐emission scanning electron microscopy, X‐ray diffraction, energy‐dispersive X‐ray spectroscopy, and atomic absorption spectroscopy. By using this catalyst system, various types of primary and secondary amines reacted with different types of aryl halides, even fluorobenzene. This catalyst can also efficiently transform all types of haloarenes into biaryl derivatives by Ullmann reaction at room temperature. Therefore, it is a promising catalyst in the area of C−F bond activation. The catalyst was reused several times and no significant loss of activity was observed.
中文翻译：
钯固定在功能化的磁性纳米粒子上，作为用于芳基卤化物的胺化和室温乌尔曼同质偶联的稳健催化剂：围绕CF键活化的过程
给出了未活化的芳基卤化物（氟苯）的布赫瓦尔德-哈特维格和乌尔曼均偶联的非均相催化活性体系的第一个例子。通过将钯离子固定在氨基吡啶官能化的Fe 3 O 4上，合成了新型的磁性非均相钯催化剂。通过FTIR光谱，程序升温还原，热重分析，CHN元素分析，透射电子显微镜，场发射扫描电子显微镜，X射线衍射，能量色散X射线光谱和原子吸收光谱对催化剂进行了全面表征。通过使用这种催化剂体系，各种类型的伯胺和仲胺与不同类型的芳基卤化物，甚至是氟苯反应。该催化剂还可以在室温下通过Ullmann反应将所有类型的卤代芳烃有效地转化为联芳基衍生物。因此，它是CF键活化领域的有希望的催化剂。催化剂被重复使用了几次，没有观察到明显的活性损失。
更新日期：2018-02-23
中文翻译：
钯固定在功能化的磁性纳米粒子上，作为用于芳基卤化物的胺化和室温乌尔曼同质偶联的稳健催化剂：围绕CF键活化的过程
给出了未活化的芳基卤化物（氟苯）的布赫瓦尔德-哈特维格和乌尔曼均偶联的非均相催化活性体系的第一个例子。通过将钯离子固定在氨基吡啶官能化的Fe 3 O 4上，合成了新型的磁性非均相钯催化剂。通过FTIR光谱，程序升温还原，热重分析，CHN元素分析，透射电子显微镜，场发射扫描电子显微镜，X射线衍射，能量色散X射线光谱和原子吸收光谱对催化剂进行了全面表征。通过使用这种催化剂体系，各种类型的伯胺和仲胺与不同类型的芳基卤化物，甚至是氟苯反应。该催化剂还可以在室温下通过Ullmann反应将所有类型的卤代芳烃有效地转化为联芳基衍生物。因此，它是CF键活化领域的有希望的催化剂。催化剂被重复使用了几次，没有观察到明显的活性损失。
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