Heck and oxidative boron Heck reactions employing Pd(II) supported amphiphilized polyethyleneimine‐functionalized MCM‐41 (MCM‐41@aPEI‐Pd) as an efficient and recyclable nanocatalyst |
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| Authors: | Fatemeh Ashori Alireza Samzadeh‐Kermani Hosein Hamadi Mohammad Reza Ganjali Hamideh Aghahosseini Ali Ramazani Mehdi Khoobi Elham Gholibegloo |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran;2. Department of Chemistry, Faculty of Sciences, University of Zabol, Zabol, Iran;3. Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz, Iran;4. Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran, Iran;5. Biosensor Research Center, Endocrinology & Metabolism Molecular‐Cellular Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran;6. Department of Chemistry, University of Zanjan, Zanjan, Iran;7. Nanobiomaterials Group, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran;8. Department of Pharmaceutical Biomaterials and Medical Biomaterials Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran |
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| Abstract: | A novel nanocatalyst was developed based on covalent surface functionalization of MCM‐41 with polyethyleneimine (PEI) using 3‐(2,3‐Epoxypropoxy)propyl] trimethoxysilane (EPO) as a cross‐linker. Amine functional groups on the surface of MCM‐41 were then conjugated with iodododecane to render an amphiphilic property to the catalyst. Palladium (II) was finally immobilized onto the MCM‐41@PEI‐dodecane and the resulted MCM‐41@aPEI‐Pd nanocatalyst was characterized by FT‐IR, TEM, ICP‐AES and XPS. Our designed nanocatalyst with a distinguished core‐shell structure and Pd2+ ions as catalytic centers was explored as an efficient and recyclable catalyst for Heck and oxidative boron Heck coupling reactions. In Heck coupling reaction, the catalytic activity of MCM‐41@aPEI‐Pd in the presence of triethylamine as base led to very high yields and selectivity. Meanwhile, the MCM‐41@aPEI‐Pd as the first semi‐heterogeneous palladium catalyst was examined in the C‐4 regioselective arylation of coumarin via the direct C‐H activation and the moderate to excellent yields were obtained toward different functional groups. Leaching test indicated the high stability of palladium on the surface of MCM‐41@aPEI‐Pd as it could be recycled for several runs without significant loss of its catalytic activity. |
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| Keywords: | Heck coupling reaction mesoporous structure oxidative boron Heck coupling reaction palladium polyethyleneimine |
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