Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 23, Pages 14234-14244Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02429
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Funding
- National Science Foundation (NSF) [CHE1465131]
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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 beta-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.
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