Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds
Abstract
:1. Introduction
2. Results and Discussion
2.1. Catalyst Characterization
2.2. Friedel–Crafts Sulfonylation
3. Materials and Methods
3.1. General Procedure for Preparation of Heterogeneous Catalyst Fe3O4@O2Si[PrMIM]Cl·AlCl3
3.1.1. The Preparation of MNPs via the Modified Chemical Coprecipitation Method
3.1.2. The Preparation of 3-Methyl-1-(3-trimethoxysilylpropyl)-1H-imidazole-3-ium Chloride
3.1.3. Methyl-1-(3-trimethoxysilylpropyl)-1H-imidazole-3-ium Chloride
3.1.4. The Preparation of Fe3O4@O2Si[PrMIM]Cl
3.1.5. The Preparation of Fe3O4@O2Si[PrMIM]Cl·AlCl3
3.2. General Procedure for the Friedel–Crafts Sulfonylation
3.3. Spectroscopic Data
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Entry | Acidic Catalyst | Ratio of 3a:3a′:3a″ | Yield (%) b |
---|---|---|---|
1 | Fe3O4@O2Si[PrMIM]HSO4 (0.2 g) | 56:41:3 | 63 |
2 | MgFe2O4@O2Si[PrMIM]Cl·AlCl3 (0.2 g) | 63:31:6 | 57 |
3 | Fe3O4@O2Si[PrMIM]Cl·AlCl3 (0.1 g) | 49:44:7 | 78 |
4 | Fe3O4@O2Si[PrMIM]Cl·AlCl3 (0.2 g) | 55:39:6 | 85 |
5 | Fe3O4@O2Si[PrMIM]Cl·AlCl3 (0.3 g) | 47:46:7 | 86 |
Entry | Arene | Sulfonyl Chloride | Product | Isolated Yield (%) (Time) d |
---|---|---|---|---|
1 | 92 (4.0) | |||
2 | 85 (4.5) | |||
3 | 67 (4.0) | |||
4 | 30 (5.0) | |||
5 | 85 (4.0) | |||
6 | 91 (1.0) | |||
7 | 89 (4.0) | |||
8 | 54 (1.0) | |||
9 | 39 (3.5) | |||
10 | 28 [e] (3.0) | |||
11 | 23 [e] (4.0) | |||
12 | 18 [e] (4.0) | |||
13 | 29 [e] (4.5) | |||
14 | 61 (2.5) | |||
15 | 79 (4.0) | |||
16 | 85 (4.0) | |||
17 b | 90 (3.0) | |||
18 b | 83 (4.0) | |||
19 | 35 (5.0) | |||
20 c | 71 (6.0) | |||
21 c | 59 (4.0) |
Entry | Arene | Product | Isolated Yield (%) (Time) c |
---|---|---|---|
1 | 76 (3.0) | ||
2 b | 73 (1.5) | ||
3 | 77 (2.0) | ||
4 | 72 (2.0) | ||
5 | 77 (3.0) | ||
6 b | 82 (2.0) | ||
7 b | 83 (2.0) | ||
8 b | 61 (2.5) | ||
9 b | 81 (2.0) |
Catalyst | X | Method | Solvent | Temp a (°C) | Time (h) | Recyclable Times | Yield b (%) | Ref. |
---|---|---|---|---|---|---|---|---|
Indium (0.2 eq) | Cl | Stirring | Dioxane | 100 | 1.5–3.0 | None | 76–84 | [28] |
Ps-AlCl3 (0.15 eq) | Cl | Stirring | Arene | 85 | 1.1–2.3 | 4 | 89–93 | [35] |
SiO2-AlCl3 (0.1 eq) | Cl | Stirring | Arene | 85 | 1.0–2.0 | 4 | 91–95 | [35] |
SiO2-AlCl3 (0.1 eq) | OH | Stirring | None | 80 | 1.3–1.9 | 4 | 88–94 | [36] |
[BTBA]FeCl3 (1 eq) | Cl | Stirring | None | 60 | 0.02–0.08 | None | 90–97 | [38] |
MoO2Cl2 (20 mol%) | Cl | Reflux | Arene | 20 | None | 44–89 | [29] | |
Cu(OTf)2, Sn(OTf)2 (5–10% mol) | Cl | Heating | Arene | 120 | 8–12 | None | 37–98 | [30] |
Fe(III)-exchanged montmorillonite (0.2 g) | OH | Reflux | Arene | 6–24 | None | 60–63 | [62] | |
OTs | Reflux | Arene | 6.0 | None | 82–94 | |||
Nafion-H (50 wt %) | OH | Reflux | Arene | 8–20 | None | 40–82 | [33] | |
Fe(OH)3 (0.1 g) | Cl | Stirring | Arene | 130–160 | 0.5–3.0 | None | 74–88 | [32] |
P2O5/Al2O3 (0.67 g) | OH | Reflux | Arene | 1.0 | None | 55–90 | [39] | |
P2O5/SiO2 (1.2 g) | OH | Reflux | Arene | 0.5–1.8 | None | 50–90 | [40] | |
Fe3O4@O2Si[PrMIM]Cl·AlCl3 (0.2 g) | Cl | Heating | None | 110 | 1.0–5.0 | 4 | 30–92 | [Our work] |
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Nguyen, N.-L.T.; Nguyen, Q.-A.; Le, T.K.; Luu, T.X.T.; Tran, K.-N.T.; Pham, P.-B. Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds. Molecules 2022, 27, 1644. https://doi.org/10.3390/molecules27051644
Nguyen N-LT, Nguyen Q-A, Le TK, Luu TXT, Tran K-NT, Pham P-B. Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds. Molecules. 2022; 27(5):1644. https://doi.org/10.3390/molecules27051644
Chicago/Turabian StyleNguyen, Ngoc-Lan Thi, Quoc-Anh Nguyen, Tien Khoa Le, Thi Xuan Thi Luu, Kim-Ngan Thi Tran, and Phuoc-Bao Pham. 2022. "Chloroaluminate Ionic Liquid Immobilized on Magnetic Nanoparticles as a Heterogeneous Lewis Acidic Catalyst for the Friedel–Crafts Sulfonylation of Aromatic Compounds" Molecules 27, no. 5: 1644. https://doi.org/10.3390/molecules27051644