General Approach to Silica-Supported Salens and Salophens and Their Use as Catalysts for the Synthesis of Cyclic Carbonates from Epoxides and Carbon Dioxide

Ryan E. Barker, Liping Guo, Claudio J.A. Mota, Michael North*, Leonardo P. Ozorio, William Pointer, Sarah Walberton, Xiao Wu

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


General routes for the synthesis of silica-immobilized symmetrical and unsymmetrical salophen and salen ligands and metal complexes have been developed starting from the natural product 4-allylanisole (methyl-chavicol and estragole). The key step of the syntheses is a microwave-assisted, platinum oxide catalyzed hydrosilylation of the terminal alkene of 5-allyl-2-hydroxybenzaldehyde to afford a sol-gel precursor which can be immobilized into silica before or after conversion to salen and salophen ligands to afford unsymmetrical and symmetrical silica-supported ligands, respectively. Both the symmetrical and unsymmetrical silica-supported salophens were found to catalyze the formation of cyclic carbonates from epoxides and carbon dioxide with catalytic activities at least comparable to those previously reported for non-immobilized homogeneous salophens. This reaction could also be carried out in a multi-phase flow reactor using ethyl acetate solutions of 3-phenoxypropylene oxide. Metal complexes of the silica-immobilized ligands could be prepared, and the aluminum complexes were also found to catalyze cyclic carbonate formation.

Original languageEnglish
Pages (from-to)16410-16423
JournalJournal of Organic Chemistry
Issue number24
Early online date1 Dec 2022
Publication statusPublished - 16 Dec 2022

Bibliographical note

© 2022 The Authors. Published by American Chemical Society.

Funding Information:
Royal Society International Collaboration Award IC170051 to MN and CJAM. Chinese Scholarship Council Award 201908330607 to LG

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