Formal Insertion of Alkenes Into C (sp 3)−F Bonds Mediated by Fluorine‐Hydrogen Bonding
Abstract: C−F Insertion reactions represent an attractive approach to prepare valuable fluorinated compounds. The high strength of C−F bonds and the low reactivity of the fluoride released upon C−F bond cleavage, however, mean that examples of such processes are extremely scarce in the literature. Here we report a reaction system that overcomes these challenges using hydrogen bond donors that both activate C−F bonds and allow for downstream reactions with fluoride. In the presence of hexafluoroisopropanol, benzyl and propargyl fluorides undergo efficient formal C−F bond insertion across α‐fluorinated styrenes. This process, which does not require any additional fluorinating reagent, occurs under mild conditions and delivers products featuring the gem‐difluoro motif, which is attracting increasing interest in medicinal chemistry. Moreover, readily available organic bromides can be engaged directly in a one‐pot process that avoids the isolation of organic fluorides.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Formal Insertion of Alkenes Into C (sp 3)−F Bonds Mediated by Fluorine‐Hydrogen Bonding ; day:11 ; month:05 ; year:2023 ; extent:8
Angewandte Chemie / International edition. International edition ; (11.05.2023) (gesamt 8)
- Urheber
- DOI
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10.1002/anie.202302860
- URN
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urn:nbn:de:101:1-2023051215020644885801
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 11:00 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Garg, Arushi
- Gerwien, Nils J.
- Fasting, Carlo
- Charlton, Alex
- Hopkinson, Matthew
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