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Copper Immobilization on Fe3O4@Agar: An Efficient Superparamagnetic Nanocatalyst for Green Ullmann-Type Cross-Coupling Reaction of Primary and Secondary Amines with Aryl Iodide Derivatives

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Abstract

Immobility of copper on magnetic nanoparticles was performed using surface rectification of Fe3O4 with Agar. The magnetic Fe3O4@Agar–Cu nanocatalyst was prepared and entirely characterized by different analyses such as Fourier transform infrared, X‐ray diffraction, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometry, energy dispersive X-ray, thermogravimetric, and inductively coupled plasma. The nanocatalyst was applied to C–N bond forming Ullmann-type Cross-Coupling reaction between aryl halides and primary or secondary amines using water as a green medium. The results of the Ullmann Cross-Coupling reaction by Fe3O4@Agar–Cu magnetic nanoparticles as catalyst demonstrate excellent activity and stability in water. Moreover, this catalyst can be recycled several times without considerable loss in its activity.

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7,7-dimethyl-5-oxo-4-phenyl-2-(phenylamino)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (Table 2, entry 16): white solid: mp 208–212 °C. 1H NMR (300 Hz, CDCl3) δ (ppm): 1.21 (s, 6H, CH3), 1.80 (s,1H,CH), 2.58 (s,2H,CH2), 3.30 (s, 2H, CH2), 7.23–7.62 (m, 10H, Ar–H). 13C NMR (75 MHz, CDCl3) δ (ppm): 195.1, 150.9, 131.2, 130.6, 129.0, 128.8, 128.5, 127.5, 119.4, 115.0, 58.3, 53.1, 43.6, 33.2, 30.9, 28.2.

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Acknowledgements

The authors gratefully acknowledge the Research Council of Ferdowsi University of Mashhad (3/52357).

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  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran

    Kimia Hoseinzade, Seyed Ali Mousavi-Mashhadi & Ali Shiri

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  1. Kimia Hoseinzade
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Correspondence to Ali Shiri.

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Hoseinzade, K., Mousavi-Mashhadi, S.A. & Shiri, A. Copper Immobilization on Fe3O4@Agar: An Efficient Superparamagnetic Nanocatalyst for Green Ullmann-Type Cross-Coupling Reaction of Primary and Secondary Amines with Aryl Iodide Derivatives. J Inorg Organomet Polym 31, 4648–4658 (2021). https://doi.org/10.1007/s10904-021-02106-x

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