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Synlett 2019; 30(06): 699-702
DOI: 10.1055/s-0037-1612076
DOI: 10.1055/s-0037-1612076
letter
An Efficient and Reusable Multifunctional Composite Magnetic Nanocatalyst for Knoevenagel Condensation
This work was supported by the National Natural Science Foundation of China (21506115) and Excellent Dissertation of China Three Gorges University (2018SSPY055).Further Information
Publication History
Received: 25 November 2018
Accepted after revision: 21 December 2018
Publication Date:
06 March 2019 (online)
Abstract
A range of multifunctional magnetic metal–organic framework nanomaterials consisting of various mass ratios of the metal–organic framework MIL-53(Fe) and magnetic SiO2@NiFe2O4 nanoparticles were designed, prepared, characterized, and evaluated as heterogeneous catalysts for the Knoevenagel condensation. The as-fabricated nanomaterials, especially the nanocatalyst MIL-53(Fe)@SiO2@NiFe2O4(1.0), showed good catalytic performance in the Knoevenagel condensation at room temperature as a result of synergistic interaction between the Lewis acid iron sites of MIL-53(Fe) and the active sites of the magnetic SiO2@NiFe2O4 nanoparticles. In addition, the heterogeneous catalyst was readily recovered and a recycling test showed that it could be reused for five times without significant loss of its catalytic activity, making it economical and environmentally friendly.
Key words
metal-organic frameworks - magnetic nanocatalyst - Knoevenagel condensation - cooperative catalysis - heterogeneous catalysis - iron catalysisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612076.
- Supporting Information
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- 38 2-Benzylidenemalononitrile; Typical ProcedureA mixture of PhCHO (5 mmol), malononitrile (5 mmol), EtOH (15 mL), and MIL-53(Fe)@SiO2@NiFe2O4(1.0) (0.1 g) was magnetically stirred at r.t. until the reaction was complete (TLC). The catalyst that precipitated out from the mixture was collected by using an external magnet, washed with EtOH, and reused for consecutive cycles under the same reaction conditions. The product was crystallized from EtOH to give a white solid; yield: 755 mg (98%); mp 83.8–84.1 °C. 1H NMR (400 MHz, CDCl3): δ = 7.47–7.64 (m, 3 H, Ar-H), 7.78 (s, 1 H, CH), 7.85–7.94 (m, 2 H, Ar-H). MS: m/z [M + H]+ calcd for C10H7N2: 155.1; found: 155.06; Anal. Calcd for C10H6N2: C, 77.87; H, 3.90; N, 18.15. Found: C, 77.91; H, 3.92; N, 18.17.