Cycloaddition Reactions of Epoxides and CO2 Catalyzed by Bifunctional Rare‐Earth Metal Complexes Bearing Amino‐Bridged Tris(phenolato) Ligands

Author:

Chen Yongjie1,Wang Yanwei1,Nong Jun1,Yuan Dan1,Yao Yingming1

Affiliation:

1. Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science Dushu Lake Campus, Soochow University Suzhou Jiangsu 215123 China

Abstract

Comprehensive SummaryEight zwitterionic rare earth metal complexes stabilized by amino‐bridged tris(phenolato) ligands bearing quaternary ammonium side‐arms were synthesized and characterized. These complexes were used as single‐component catalysts for the cycloaddition of CO2 and epoxides, and their catalytic activities are obviously higher than those of their binary analogues. Further studies revealed that the halide anions (Cl, Br, I) and the metal complexes influenced the catalytic activity, and the lanthanum complex bearing iodide anion showed the highest catalytic activity for this addition reaction. A variety of mono‐substituted epoxides were converted to cyclic carbonates in good to excellent yields (55%—99%) with high selectivity (> 99%) at 30 °C and 1 bar CO2, whereas internal epoxides required higher both reaction temperatures (60—120 °C) and catalyst loading (2 mol%) for high yields. The catalyst was recyclable for four times without noticeable loss of catalytic activity. Based on the results of kinetic studies and in situ IR reactions, a plausible reaction mechanism was proposed.

Funder

National Key Research and Development Program of China

National Natural Science Foundation of China

Priority Academic Program Development of Jiangsu Higher Education Institutions

Publisher

Wiley

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