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. 2022 Sep 1;12(1):14865.
doi: 10.1038/s41598-022-19030-w.

A diselenobis-functionalized magnetic catalyst based on iron oxide/silica nanoparticles suggested for amidation reactions

Reza Taheri-Ledari  1 , Fateme Sadat Qazi  1 , Mahdi Saeidirad  1 , Ali Maleki  2
Affiliations

A diselenobis-functionalized magnetic catalyst based on iron oxide/silica nanoparticles suggested for amidation reactions

Reza Taheri-Ledari et al. Sci Rep. .

Abstract

In this study, a new heterogeneous magnetic catalytic system based on selenium-functionalized iron oxide nanoparticles is presented and suggested for facilitating amide/peptide bonds formation. The prepared nanocatalyst, entitled as "Fe3O4/SiO2-DSBA" (DSBA stands for 2,2'-diselanediylbis benzamide), has been precisely characterized for identifying its physicochemical properties. As the most brilliant point, the catalytic performance of the designed system can be mentioned, where only a small amount of Fe3O4/SiO2-DSBA (0.25 mol%) has resulted in 89% reaction yield, under a mild condition. Also, given high importance of green chemistry, convenient catalyst particles separation from the reaction medium through its paramagnetic property (ca. 30 emu·g-1) should be noticed. This particular property provided a substantial opportunity to recover the catalyst particles and successfully reuse them for at least three successive times. Moreover, due to showing other excellences, such as economic benefits and nontoxicity, the presented catalytic system is recommended to be scaled up and exploited in the industrial applications.

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Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Reactions that take place in different stages of the synthesis of 2,2′-diselanediyldibenzoic acid.
Figure 2
Figure 2
Digital images of: (a) synthesis of K2Se2 metal salt, (b) synthesis of 2-carboxybenzenediazonium chloride, (c) synthesis of 2,2′-diselanediyldibenzoic acid (N2 release creates the bubbles), (d) synthesis of 2,2′-diselanediyldibenzoic acid after stirring for 2 h at 90 °C, (e) filtered unreacted selenium and oxidized selenium by celite pad, and filtrate including 2,2′-diselanediyldibenzoic acid, and (f) 2,2′-diselanediyldibenzoic acid sediment after addition of hydrochloric acid (1 M) (recrystallization has been presented in Video #1).
Figure 3
Figure 3
Schematic presentation of the preparation route of Fe3O4@SiO2-DSBA catalytic system.
Figure 4
Figure 4
EDX spectra of (a) Fe3O4, (b) Fe3O4@SiO2, (c) Fe3O4@SiO2-NH2, and (d) Fe3O4/SiO2-DSBA.
Figure 5
Figure 5
VSM curves of Fe3O4/SiO2-DSBA nanoparticles (red) and Fe3O4/SiO2 nanoparticles (black).
Figure 6
Figure 6
XRD pattern of: (a) Fe3O4/SiO2-DSBA catalytic system, (b) SiO2 NPs, and (c) Fe3O4 NPs. NP: new peaks, are attributed to the new crystalline phase formed onto the surfaces of the Fe3O4/SiO2 NPs after functionalization with DSBA.
Figure 7
Figure 7
(a) TGA curve and (b) DTA curve of the designed Fe3O4/SiO2-DSBA catalytic system, under argon atmosphere.
Figure 8
Figure 8
FESEM images of (a) Fe3O4 NPs, (b) Fe3O4/SiO2 NPs, (c) Fe3O4/SiO2-DSBA, (d–f) TEM image of Fe3O4/SiO2-DSBA catalytic system, and (g-series) SEM energy-mapping of Fe3O4/SiO2-DSBA catalytic system.
Figure 9
Figure 9
(a) 1HNMR of 2,2′-diselenobis benzoic acid. (b) 13CNMR of 2,2′-diselenobis benzoic acid.
Figure 10
Figure 10
(a) Recyclability investigation of Fe3O4/SiO2-DSBA nanoparticles in catalyzed peptide coupling reactions. The results were obtained from the coupling reaction between glycine methyl ester and Fmoc-protected phenyl alanine, per 0.25 mol% of the catalyst at room temperature, (b) EDX data, (c) SEM image, and (d) FTIR spectrum of the recovered Fe3O4/SiO2-DSBA nanoparticles after six times recycles.
Figure 11
Figure 11
A plausible mechanism suggested for the catalyzed amidation reaction by Fe3O4/SiO2-DSBA catalytic system.
See this image and copyright information in PMC

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