Dramatic Influence of Ionic Liquid and Ultrasound Irradiation on the Electrophilic Sulfinylation of Aromatic Compounds by Sulfinic Esters
Abstract
:1. Introduction
2. Results
3. Discussion
4. Materials and Methods
4.1. Instrumentation
4.2. Chemicals
4.3. General Procedure for the Sulfinylation of Aromatic Compound with Sulfinic Ester under Ultrasound Irradiation
4.4. Spectroscopic Data
5. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Sample Availability: Not available. |
Entry | Acidic Catalyst (mmol) | Yield b (%) |
---|---|---|
1 | Bi(OTf)3(0.05), solvent-free | 3 |
2 | La(OTf)3(0.05), solvent-free | - |
3 | Cu(OTf)2(0.05), solvent-free | - |
4 | AlCl3(2.0), solvent-free | 16 |
5 | AlCl3(2.0) in 1,2-dichloroethane (1 mL) | 7 |
6 | [(HSO3)4C4C1Im]HSO4(1.0) | 6 |
7 | [Choline]Cl·3ZnCl2 (1.0) | - |
8 | [Bmim]Cl·2ZnCl2 (1.0) | 3 |
9 | [Bmim]Cl·2ZnCl2 (1.2) | 4 |
10 | [Bmim]Cl·2NiCl2(1.0) | - |
11 | [Bmim]Cl·p-TSA (2.0) | - |
12 | [Bmim]Cl·AlCl3(1.0) | 32 |
13 | [Bmim]Cl·2AlCl3(1.0) | 55 |
14 | [Bmim]Cl·3AlCl3(1.0) | 25 |
15 | [Bmim]Cl·2AlCl3(1.1) | 69 |
16 | [Bmim]Cl·2AlCl3(1.2) | 72 |
17 | [Bmim]Cl·2AlCl3(1.5) | 68 |
Entry | Sulfinic Ester | Product | Time (h) | Yield b (%) | |
---|---|---|---|---|---|
1 | 3a | 1.0 1.5 | 72 73 | ||
2 | 1.0 | 72 | |||
3 | 1.0 | 77 | |||
4 | 3b | 1.0 4.0 | 15 70 | ||
5 | 3c | 1.0 4.5 | 10 68 | ||
6 | 3d | 1.0 4.0 | 17 72 | ||
7 | 3e | 1.0 | 73 | ||
8 | 3f | 1.0 | 75 |
Entry | Arene | Product | Time (h) | Yield b (%) | |
---|---|---|---|---|---|
1 | 3g | 1.0 | 61 | ||
2 | 3h | 1.0 | 68 | ||
3 | 1.0 | 75 | |||
4 | 3j | 1.0 | 81 | ||
5 | 3k | 2.0 | 58 | ||
6 | 3l | 3.0 | 53 | ||
7 | 3m | 0.5 | 73 | ||
8 | 3n | 0.5 | 40 | ||
9 | 3p | 8 | 13 | ||
10 | 3q | 8 | 6 |
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Nguyen, N.-L.T.; Vo, H.-T.; Duus, F.; Luu, T.X.T. Dramatic Influence of Ionic Liquid and Ultrasound Irradiation on the Electrophilic Sulfinylation of Aromatic Compounds by Sulfinic Esters. Molecules 2017, 22, 1458. https://doi.org/10.3390/molecules22091458
Nguyen N-LT, Vo H-T, Duus F, Luu TXT. Dramatic Influence of Ionic Liquid and Ultrasound Irradiation on the Electrophilic Sulfinylation of Aromatic Compounds by Sulfinic Esters. Molecules. 2017; 22(9):1458. https://doi.org/10.3390/molecules22091458
Chicago/Turabian StyleNguyen, Ngoc-Lan Thi, Hong-Thom Vo, Fritz Duus, and Thi Xuan Thi Luu. 2017. "Dramatic Influence of Ionic Liquid and Ultrasound Irradiation on the Electrophilic Sulfinylation of Aromatic Compounds by Sulfinic Esters" Molecules 22, no. 9: 1458. https://doi.org/10.3390/molecules22091458