Preparation of Metal-Immobilized Methacrylate-Based Monolithic Columns for Flow-Through Cross-Coupling Reactions

• Published in: Molecules (Basel, Switzerland) Vol. 26; no. 23; p. 7346
• Main Authors: Sabarudin, Akhmad, Shu, Shin, Yamamoto, Kazuhiro, Umemura, Tomonari
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 03.12.2021; MDPI
• Subjects: Acids; By products; catalyst; Catalysts; Chemical reactions; Cross coupling; Efficiency; flow-through reaction; Iminodiacetic acid; Ligands; microreactor; Microreactors; monolith; Palladium; Phosphonic acids; polymer; Pore size; Porosity; Porous materials; Solvents
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules26237346

With the aim of developing efficient flow-through microreactors for high-throughput organic synthesis, in this work, microreactors were fabricated by chemically immobilizing palladium-, nickel-, iron-, and copper-based catalysts onto ligand-modified poly(glycidyl methacrylate-co-ethylene dimethacrylate) [poly(GMA-co-EDMA)] monoliths, which were prepared inside a silicosteel tubing (10 cm long with an inner diameter of 1.0 mm) and modified with several ligands including 5-amino-1,10-phenanthroline (APHEN), iminodiacetic acid (IDA), and iminodimethyl phosphonic acid (IDP). The performance of the resulting microreactors in Suzuki−Miyaura cross-coupling reactions was evaluated, finding that the poly(GMA-co-EDMA) monolith chemically modified with 5-amino-1,10-phenanthroline as a binding site for the palladium catalyst provided an excellent flow-through performance, enabling highly efficient and rapid reactions with high product yields. Moreover, this monolithic microreactor maintained its good activity and efficiency during prolonged use.