Fluorofunctionalization of C═C Bonds with Selectfluor: Synthesis of β-Fluoropiperazines through a Substrate-Guided Reactivity Switch
| Autor: | Thomas Lectka, Wei Hao Lee, Joseph N. Capilato, Rayyan Trebonias Jokhai, Louis E. S. Hoffenberg, Desta Doro Bume |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Alkene Organic Chemistry Heteroatom Regioselectivity Ammonium fluoride 010402 general chemistry 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry Reagent Reactivity (chemistry) Selectfluor Fluoride |
| Zdroj: | The Journal of organic chemistry. 83(23) |
| ISSN: | 1520-6904 |
| Popis: | The halofunctionalization of alkene substrates remains an essential tool for synthetic chemists. Herein, we report regioselective ammoniofluorination of unactivated alkenes through photochemical means. A one-pot transformation of the ammonium fluoride products into pharmaceutically relevant β-fluoropiperazines is highlighted. Furthermore, a substrate-guided reactivity switch is observed: certain alkenes are shown to react with the same fluorinating reagent to instead give the less-substituted fluoride. We hope that the ammoniofluorination reaction will be of utility in the area of medicinal chemistry, where nitrogen and fluorine are among the most important heteroatoms. |
| Databáze: | OpenAIRE |
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