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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 Publisher



Motevalizadeh SF1 ; Alipour M2 ; Ashori F3 ; Samzadehkermani A4 ; Hamadi H5 ; Ganjali MR6, 7 ; Aghahosseini H8 ; Ramazani A8 ; Khoobi M2, 9 ; Gholibegloo E8
Authors
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Authors Affiliations
  1. 1. Particulate Fluids Processing Centre, School of Chemistry, The University of Melbourne, Melbourne, 3010, VIC, Australia
  2. 2. Nanobiomaterials Group, Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, 1417614411, Iran
  3. 3. Department of Applied Chemistry, Faculty of Pharmaceutical Chemistry, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran
  4. 4. Department of Chemistry, Faculty of Sciences, University of Zabol, Zabol, Iran
  5. 5. Department of Chemistry, College of Science, Shahid Chamran University, Ahvaz, Iran
  6. 6. Center of Excellence in Electrochemistry, Faculty of Chemistry, University of Tehran, Tehran, Iran
  7. 7. Biosensor Research Center, Endocrinology & Metabolism Molecular-Cellular Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  8. 8. Department of Chemistry, University of Zanjan, P.O. Box 45195-313, Zanjan, Iran
  9. 9. Department of Pharmaceutical Biomaterials and Medical Biomaterials Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Applied Organometallic Chemistry Published:2018


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. Copyright © 2017 John Wiley & Sons, Ltd.