Regioselective Electrophilic Fluorination of Rationally Designed Imidazole Derivatives
| Autor: | Klaus Albertshofer, Neelakandha S. Mani |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Organic Chemistry Electrophilic fluorination Regioselectivity 010402 general chemistry 01 natural sciences Chemical reaction 0104 chemical sciences chemistry.chemical_compound Deprotonation chemistry Molecule Imidazole Organic chemistry Lewis acids and bases Protecting group |
| Zdroj: | The Journal of organic chemistry. 81(3) |
| ISSN: | 1520-6904 |
| Popis: | We report the regioselective and direct functionalization of rationally designed imidazole derivatives through electrophilic fluorination with N-fluorobenzenesulfonimide enabled via in situ deprotonation with lithium 2,2,6,6-tetramethylpiperidine. Aided by a controlled protecting group switch, we were able to effectively target both the reactive 5- as well as the difficult to target 4-position of these molecules, leading to a series of fluorinated polysubstituted imidazoles in gram scale. |
| Databáze: | OpenAIRE |
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