Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination
Abstract
:1. Introduction
2. Result and Discussion
3. Materials and Methods
3.1. Procedure of Nucleophilic Fluorinations in Table 1
3.2. Procedure of Fluorination of Various Substrates and Analytical Data of Fluorination Products in Table 2
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Entry | Promoter (Equiv) | Solvent | MF | Time (h) | Yield b | |||
---|---|---|---|---|---|---|---|---|
3 | 4a | 4b | 4c | |||||
1 | PCLS-hexaEGIM (0.3) | CH3CN | CsF | 2 | - | 97 (94) c | - | - |
2 | - | CH3CN | CsF | 10 | 90 | 10 | - | - |
3 | PCLS-hexaEGIM (0.3) | CH3CN | NaF | 24 | 75 | 20 | 5 | - |
4 | PCLS-hexaEGIM (0.3) | CH3CN | KF | 10 | - | 94 | 5 | - |
5 | PCLS-hexaEGIM (0.3) | CH3CN | RbF | 9 | 3 | 92 | 5 | - |
6 | PCLS-hexaEGIM (0.3) | Benzene | CsF | 12 | - | 85 | 15 | - |
7 | PCLS-hexaEGIM (0.3) | 1,4-dioxane | CsF | 12 | - | 88 | 12 | - |
8 | PCLS-hexaEGIM (0.3) | DMF | CsF | 3 | - | 90 | 10 | - |
9 | PCLS-hexaEGIM (0.3) | t-amyl alcohol | CsF | 45 min | - | 98 | - | - |
10 d | - | t-amyl alcohol | CsF | 2.5 | - | 94 | - | - |
11 | 18-crown-6 (0.5) | CH3CN | CsF | 8 | 10 | 65 | 5 | 25 |
12 | PS[hmim][BF4] (0.5) | CH3CN | CsF | 5 | 94 | - | 6 | |
13 | hexaEGVIM 2 (0.5) | CH3CN | CsF | 5 | - | 92 | - | 8 |
Entry | Structure of Product | X | Solvent | Time (h) | Yield (%) b | Comments |
---|---|---|---|---|---|---|
1 | Br | CH3CN | 4 | 75 c | 15% alkenes 10% alcohol | |
2 d | Br | t-amyl alcohol | 2 | 94 c | 3% alkenes trace alcohol | |
3 | OMs | CH3CN | 3 | 80 c | 20% alkenes | |
4 | OMs | t-amyl alcohol | 1.5 | 95 c | 5% alkenes | |
5 | OMs | CH3CN | 2 | 80 c | 15% alkenes 5% alcohol | |
6 | OMs | t-amyl alcohol | 0.5 | 95 c | 5% alkenes | |
7 | OMs | CH3CN | 2 | 93 | 4% alcohol | |
8 | Br | CH3CN | 3 | 90 | 6% alkenes | |
9 | I | CH3CN | 3 | 91 | 4% alkenes | |
10 | Br | CH3CN | 1 | 94 | - | |
11 | OMs | CH3CN | 0.75 | 96 | - | |
12 | Br | CH3CN | 0.5 | 90 | 4% alcohol | |
13 e | OMs | CH3CN | 1 | 96 | - | |
14 e | Cl | CH3CN | 1 | 92 | trace alcohol | |
15 | Br | CH3CN | 1 | 92 | 4% alcohol | |
16 | OMs | CH3CN | 3 | 95 | - |
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Reddy, M.V.; Park, K.H.; Kim, D.W. Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination. Molecules 2023, 28, 6747. https://doi.org/10.3390/molecules28186747
Reddy MV, Park KH, Kim DW. Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination. Molecules. 2023; 28(18):6747. https://doi.org/10.3390/molecules28186747
Chicago/Turabian StyleReddy, Mudumala Veeranarayana, Keun Heok Park, and Dong Wook Kim. 2023. "Poly Caprolactam Supported Hexaethylene Glycolic Imidazolium Ionic Liquid as a Heterogeneous Promoter for Nucleophilic Fluorination" Molecules 28, no. 18: 6747. https://doi.org/10.3390/molecules28186747