Subscribe to RSS
DOI: 10.1055/a-2182-7757
Exploring the Catalytic Efficiency of Copper-Doped Magnetic Carbon Aerogel for the Coupling Reaction of Isatin Oxime with Phenylboronic Acid Derivatives
The authors thank the Science and Engineering Research Board, New Delhi for financial support through the SERB-TARE Project (TAR/2022/000673).
Abstract
A highly efficient catalyst, Cu-doped poly(N-[3-(dimethylamino)propyl]methacrylamide, acrylic acid, N-vinyl imidazole) (PDAI) magnetic carbon aerogel (CPIMCA), was successfully employed for the synthesis of isatin nitrone derivatives. The 3D porous CPIMCA catalyst demonstrated outstanding performance through the application of a coupling reaction between isatin oxime and phenylboronic acid derivatives, providing up to 98% yield of the required nitrone derivatives. Remarkably, the incorporation of copper within the polymeric structure of the magnetic carbon aerogel exhibited a significant influence on catalytic activity, even at a low overall copper content of approximately 2%. This was confirmed through EDX elemental mapping analysis, further establishing the competence of the catalyst for catalytic reactions. Comparative studies revealed that CPIMCA outperformed Cu(Oac)2 catalyst, providing a notable 10–15% increase in product yield. This superior performance can be attributed to the unique synergistic effect of copper, iron, and carbon aerogel as the polymeric matrix, highlighting the exceptional capabilities of CPIMCA as a catalyst.
Keywords
catalytic coupling reaction - recyclable magnetic catalyst - carbon aerogel - iron - copper dopingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2182-7757.
- Supporting Information
Publication History
Received: 28 July 2023
Accepted after revision: 21 September 2023
Accepted Manuscript online:
27 September 2023
Article published online:
09 November 2023
© 2023. This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Farzaliyev V, Shuriberko A, Sujayey A, Osmanova S, Gojayeva S, Gahramanova K. J. Mol. Struct. 2020; 1221: 128844
- 2 Kaushal A, Bhukya J, Yadav AK, Mishra V, Kumar D. Tetrahedron Lett. 2023; 154742
- 3 Kumar V, Saha R, Chatterjee S, Mishra V. React. Chem. Eng. 2023; 8: 2677
- 4 Son GM, Truong CC, Mishra DK, Mishra V, Kim YJ. Bull. Korean Chem. Soc. 2018; 39: 174
- 5 Yen C.-T, Liu Y.-H, Peng S.-M, Liu S.-T. Org. Lett. 2022; 24, 3373
- 6 Dai S, Chou JP, Wang KW, Hsu YY, Hu A, Pan X, Chen TY. Nat. Commun. 2019; 10: 440
- 7 Yang Y, Reber AC, Gilliland SE. III, Castano CE, Gupton BF, Khanna SN. J. Catal. 2018; 360: 20
- 8 Fernández E, Rivero-Crespo MA, Dominguez I, Rubio-Marques P, Oliver-Meseguer J, Liu L, Cabereo-Antonino M, Gavara R, Hernandez-Garrido JC, Boronat M, Levya-Perez A. J. Am. Chem. Soc. 2019; 141: 1928
- 9 Baran T. J. Colloid Interface Sci. 2017; 496: 446
- 10 Zhang Z, Zhao Z, Hou Y, Wang H, Li X, He G, Zhang M. Angew. Chem. Int. Ed. 2019; 58: 8862
- 11 Oh SG, Mishra V, Cho JK, Kim BJ, Kim HS, Suh YW, Lee H, Park HS, Kim YJ. Catal. Commun. 2014; 43: 79
- 12 Ming X.-X, Wu S, Tian Z.-Y, Song J.-W, Zhang C.-P. Org. Lett. 2021; 23: 6795
- 13 Devendar P, Qu RY, Kang WM, He B, Yang GF. J. Agric. Food Chem. 2018; 66: 8914
- 14 Karbowska B. Environ. Monit. Assess. 2016; 188
- 15 Truong CC, Mishra DK, Mishra V. Organic carbonate as a green solvent for biocatalysis. In Green Sustainable Process for Chemical and Environmental Engineering and Science. Elsevier; Amsterdam, Netherlands: 2021: 253-275
- 16 Panda SK, Aggarwal I, Kumar H, Prasad L, Kumar A, Sharma A, Vo DV. N, Van Thuan D, Mishra V. Environ. Chem. Lett. 2021; 19: 2487
- 17 Jindal S, Anand R, Sharma N, Yadav N, Mudgal D, Mishra R, Mishra V. ACS Appl. Electron. Mater. 2022; 4: 2146
- 18 Yadav N, Gaikwad RP, Mishra V, Gawande MB. Bull. Chem. Soc. Jpn. 2022; 95: 1638
- 19 Mishra V, Cho JK, Shin SH, Suh YW, Kim HS, Kim YJ. Appl. Catal., A 2014; 487: 82
- 20 Kumar M, Verma S, Mishra V, Reiser O, Verma AK. J. Org. Chem. 2022; 87: 6263
- 21 Veerakumar P, Thanasekaran P, Subburaj T, Lin K.-C. C 2018; 4: 54
- 22 Karoyo AH, Wilson LD. Materials 2021; 14: 1095
- 23 Pekel N, Güven O. Polym. Bull. 2004; 51: 307
- 24 Mishra V, Kumar R. Carbohydr. Polym. 2011; 83: 1534
- 25 Mishra V, Jung SH, Park JM, Jeong HM, Lee HI. Macromol. Rapid Commun. 2014; 35: 442
- 26 Mishra V, Kumar R. J. Appl. Polym. Sci. 2013; 128: 3295
- 27 Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
- 28 Sharma S, Kaur M, Sharma C, Choudhary A, Paul S. ACS Omega 2021; 6: 19529
- 29 Panda N, Jena AK. Org. Chem.: Curr. Res. 2015; 4: 1000130
- 30 Shirakawa E, Ikeda D, Masui S, Yoshida M, Hayashi T. J. Am. Chem. Soc. 2012; 134: 272
- 31 Liu L, Corma A. Chem. Rev. 2018; 118: 4981
- 32 Mo XL, Chen CH, Liang C, Mo DL. Eur. J. Org. Chem. 2018; 150
- 33 Chen CH, Liu QQ, Ma XP, Feng Y, Liang C, Pan CX, Su GF, Mo DL. J. Org. Chem. 2017; 82: 6417
- 34 Arkaban H, Barani M, Akbarizadeh MR, Chauhan NP. S, Jadoun S, Soltani MD, Zarrintaj P. Polymers 2022; 14: 1259
- 35 Li Y, Huang G, Zhang X, Li B, Chen Y, Lu T, Lu TJ, Xu F. Adv. Funct. Mater. 2013; 23: 660
- 36 He X, Zhang L, Meng D, Wu J. Eur. Polym. J. 2017; 89: 461
- 37 Saczewski J, Paluchowska A, Klenc J, Raux E, Barnes S, Sullivan S, Duszynska B, Bojarski AJ, Strekowski L. J. Heterocycl. Chem. 2009; 46: 1259
- 38 Yang Z, Peng H, Wang W, Liu T. J. Appl. Polym. Sci. 2010; 116: 2658
- 39 Esfahani MZ, Aghaei A, Khosravi M, Bagheri N, Khakpour Z, Javaheri M. New J. Chem. 2017; 41: 11731
- 40 Mohsenpour M, Motahari S, Tajabadi F, Najafi M. RSC Adv. 2020; 10: 41780
- 41 Slimi O, Djouadi D, Hammiche L, Chelouche A, Touam T. J. Porous Mater. 2018; 25: 595
- 42 Ye S, Jin W, Huang Q, Hu Y, Li Y, Li B. Int. J. Biol. Macromol. 2016; 92: 1169
- 43 Andrew LJ, Gillman ER, Walters CM, Lizundia E, MacLachlan MJ. Small 2023; 2301947
- 44 Zhai Z, Ren B, Xu Y, Wang S, Zhang L, Liu Z. IOP Conf. Ser. Earth Environ. Sci. 2020; 508
- 45 Kreek K, Kulp M, Uibu M, Mere A, Koel M. Oil Shale 2014; 31: 185
- 46 Pang Y, Mo Z, Wang H, Linkov V, Wang X, Wang R. Catal. Sci. Technol. 2020; 10: 5288
- 47 Yang M, Wang H, Jin S, Zhang R, Wang Y, Huo W, Wang X, Jin M, Qiao W, Ling L. Catal. Sci. Technol. 2021; 11: 2057
- 48 Ahamad T, Naushad M, Ruksana, Alhabarah AN, Alshehri SM. Int. J. Biol. Macromol. 2019; 132: 1031
- 49 Reyhani R, Zadhoush A, Tabrizi NS, Nazockdast H, Naeimirad M. J. Non-Cryst. Solids 2021; 571: 7073
- 50 Zhai Z, Ren B, Xu Y, Wang S, Zhang L, Liu Z. Org. Electron. 2019; 70: 246
- 51 Fu R, Yoshizawa N, Dresselhaus MS, Dresselhaus G, Satcher JH, Baumann TF. Langmuir 2002; 18: 10100
- 52 Wang S, Xu Y, Yan M, Zhai Z, Ren B, Zhang L, Liu Z. J. Electroanal. Chem. 2018; 809: 111
- 53 Dong X, Xu Y, Wang S, Zhao J, Ren B, Zhang L, Liu Z. Materials 2018; 11
- 54 Byrne FP, Jin S, Paggiola G, Petchey TH, Clark JH, Farmer TJ, Hunt AJ, McElroy CR, Sherwood J. Sustainable Chem. Processes. 2016; 4