Journal
ACS APPLIED MATERIALS & INTERFACES
Volume 10, Issue 11, Pages 9478-9484Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsami.8b00485
Keywords
carbon dioxide; chemical fixation; cycloaddition; organocatalyst; heterogeneous
Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [NRF-2016R1A2B4011027, NRF-2017M3A7B4042140, NRF-2017M3A7B4042235]
- NRF [NRF-2015R1D1A4A01018697]
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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.
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