Slimani Ichraf, Özdemir İsmail, Gürbüz Nevin, Alıcı Bülent, Arslan Nahide Burcu, Özdemir Namık
Catalysis Research and Application Center, İnönü University, Malatya 44280, Turkey.
Faculty of Science and Arts, Department of Chemistry, İnönü University, Malatya 44280, Turkey.
ACS Omega. 2025 Aug 27;10(35):39994-40008. doi: 10.1021/acsomega.5c04713. eCollection 2025 Sep 9.
The formation of carbon-carbon bonds constitutes one of the most fundamental synthetic operations in organic chemistry. Arylation of heteroarenes through C-H bond activation using Pd-PEPPSI complexes as catalysts was widely performed using the classical heating method. However, the use of this heating method is associated with an unfavorable environmental profile, as they generally use a high reaction temperature, a high catalyst load, and a long reaction time. Herein, we disclose the synthesis of new Pd-PEPPSI-NHC complexes bearing NHC ligands, which were tested as a catalyst in the arylation of 2-acethylfuran and 2-acethylthiophene with different aryl bromides using microwave irradiation. This novel method provides access to the biaryl scaffolds in good yields using 0.5 mol % as catalyst loading and at 110 °C. The structure of the five palladium-(II) complexes has been elucidated through NMR H, C, and FT-IR spectroscopy. Furthermore, the square-planar geometry of the organometallic ion was confirmed by single-crystal X-ray diffraction carried out on complexes and .
碳-碳键的形成是有机化学中最基本的合成操作之一。使用钯-PEPPSI配合物作为催化剂,通过C-H键活化实现杂芳烃的芳基化反应,传统上采用经典加热方法广泛进行。然而,这种加热方法的使用与不良的环境影响相关,因为它们通常使用较高的反应温度、较高的催化剂负载量和较长的反应时间。在此,我们报道了带有N-杂环卡宾(NHC)配体的新型钯-PEPPSI-NHC配合物的合成,这些配合物在微波辐射下,作为2-乙酰基呋喃和2-乙酰基噻吩与不同芳基溴进行芳基化反应的催化剂进行了测试。这种新方法以0.5 mol%的催化剂负载量,在110°C下,能够以良好的产率获得联芳基骨架。通过核磁共振氢谱、碳谱以及傅里叶变换红外光谱对五种钯(II)配合物的结构进行了阐明。此外,通过对配合物 和 进行单晶X射线衍射,证实了有机金属离子的平面正方形几何结构。