Monodisperse [email protected] [email protected] Nanoparticles Assembled on Reduced Graphene Oxide as a Highly Efficient and Reusable Heterogeneous Catalyst for the C–H Bond Arylation of Imidazo[1,2-a]pyridine with Aryl Halides,ACS Sustainable Chemistry & Engineering

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Monodisperse [email protected] [email protected] Nanoparticles Assembled on Reduced Graphene Oxide as a Highly Efficient and Reusable Heterogeneous Catalyst for the C–H Bond Arylation of Imidazo[1,2-a]pyridine with Aryl Halides
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-07-18 00:00:00 , DOI: 10.1021/acssuschemeng.8b01431
Haydar Kilic _{1,

2,

3} , Muhammet Turgut ₁ , Melike Sevim Yilmaz ₁ , Oguzhan Dalkilic ₁ , Önder Metin ₁

Affiliation

We report herein, for the first time, the direct C–H bond arylation of imidazo[1,2-a]pyridine with aryl halides using monodisperse [email protected] [email protected] nanoparticles assembled on reduced graphene oxide (rGO) as a highly efficient and reusable heterogeneous catalyst. Monodisperse [email protected] [email protected] nanoparticles (NPs) were synthesized by using one-pot successive reduction of metal precursors in the presence of oleylamine and trioctyl phosphine and then assembled on rGO via a liquid-phase self-assembly method to yield [email protected] nanocatalyst. The structures of the colloidal [email protected] [email protected] NPs and [email protected] nanocatalyst were characterized by TEM, high-resolution TEM (HR-TEM), STEM-EDS, XPS, and ICP-MS. Next, [email protected] nanocatalysts as well as rGO-Ni and rGO-Pd counterparts were first tested in the direct C–H bond arylation of imidazo[1,2-a]pyridine with bromobenzene under tunable reaction conditions to find the optimum reaction conditions. Under the optimum reaction conditions, the substrate scope of [email protected] direct C–H arylation of imidazo[1,2-a]pyridine was examined by performing the catalytic reactions with a variety of aryl halides. These studies showed for the first time that [email protected] nanocatalysts are highly efficient and reusable catalysts in the direct C–H bond arylation reactions and have a high potential to be applied in other C–H activation reactions.

中文翻译：

单分散[受电子邮件保护] [受电子邮件保护]在还原的氧化石墨烯上组装的纳米颗粒，是咪唑并[1,2- a ]吡啶与芳基卤化物进行C–H键芳构化的高效且可重复使用的多相催化剂

我们在此首次报道了咪唑[1,2- a]的直接CH键芳基化使用在分散的氧化石墨烯（rGO）上组装的单分散[受电子邮件保护] [受电子邮件保护]纳米颗粒将吡啶与芳基卤化物作为高效且可重复使用的多相催化剂。通过在油胺和三辛基膦的存在下一锅连续还原金属前体来合成单分散[受电子邮件保护] [受电子邮件保护]纳米粒子（NP），然后通过液相自组装方法在rGO上组装以产生[受电子邮件保护的]纳米催化剂。胶体[受电子邮件保护] [受电子邮件保护] NPs和[受电子邮件保护]纳米催化剂的结构通过TEM，高分辨率TEM（HR-TEM），STEM-EDS，XPS和ICP-MS进行表征。接下来，[电子邮件保护的]纳米催化剂以及rGO-Ni和rGO-Pd对应物首先在咪唑[1,2-在可调节的反应条件下将α ]吡啶与溴苯反应以找到最佳反应条件。在最佳反应条件下，通过与多种芳基卤化物进行催化反应，对咪唑并[1,2- a ]吡啶进行[电子邮件保护]直接CHH芳基化反应的底物范围进行了研究。这些研究首次表明，[电子邮件保护的]纳米催化剂在直接的C–H键芳基化反应中是高效且可重复使用的催化剂，在其他C–H活化反应中具有很高的应用潜力。

更新日期：2018-07-18

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