Highly Efficient Catalytic Cyclic Carbonate Formation by Pyridyl Salicylimines

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Cyclic carbonates as industrial commodities offer a viable nonredox carbon dioxide fixation, and suitable heterogeneous catalysts are vital for their widespread implementation. Here, we report a highly efficient heterogeneous catalyst for CO2 addition to epoxides based on a newly identified active catalytic pocket consisting of pyridine, imine, and phenol moieties. The polymeric, metal-free catalyst derived from this active site converts less-reactive styrene oxide under atmospheric pressure in quantitative yield and selectivity to the corresponding carbonate. The catalyst does not need additives, solvents, metals, or co-catalysts, can be reused at least 10 cycles without the loss of activity, and scaled up easily to a kilogram scale. Density functional theory calculations reveal that the nucleophilicity of pyridine base gets stronger due to the conjugated imines and H-bonding from phenol accelerates the reaction forward by stabilizing the intermediate.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-03
Language
English
Article Type
Article
Citation

ACS APPLIED MATERIALS & INTERFACES, v.10, no.11, pp.9478 - 9484

ISSN
1944-8244
DOI
10.1021/acsami.8b00485
URI
http://hdl.handle.net/10203/241528
Appears in Collection
EEW-Journal Papers(저널논문)CBE-Journal Papers(저널논문)
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