Deoxytrifluoromethylation/aromatization of cyclohexan(en)ones to access highly substituted trifluoromethyl arenes
Trifluoromethyl arenes (Ar–CF 3 ) are amongst the commonly encountered fluorinated substructures in pharmaceutical, agrochemical, and material sciences. However, predominant methods to access Ar–CF 3 possess several limitations, including harsh conditions, lack of availability of substrates, and poo...
Gespeichert in:
Veröffentlicht in: | Nature communications 2024-09, Vol.15 (1), p.7882-9, Article 7882 |
---|---|
Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Trifluoromethyl arenes (Ar–CF
3
) are amongst the commonly encountered fluorinated substructures in pharmaceutical, agrochemical, and material sciences. However, predominant methods to access Ar–CF
3
possess several limitations, including harsh conditions, lack of availability of substrates, and poor regioselectivity, which combined restrict access to desirable highly functionalized Ar–CF
3
-containing compounds. To expand the scope of accessible Ar–CF
3
-based molecules, we present an orthogonal deoxyfluoroalkylation/aromatization approach that exploits readily accessible and programable cyclohexan(en)one substrates, which undergo a reliable 1,2-addition reaction with the Ruppert-Prakash reagent (TMSCF
3
) followed by aromatization to deliver highly functionalized Ar–CF
3
compounds in a one/two-pot sequence. This general strategy enables access to highly substituted Ar–CF
3
-containing molecules that are difficult, expensive, and/or impossible to access by current synthetic methods.
Trifluoromethyl arenes are amongst the commonly encountered fluorinated substructures in pharmaceutical, agrochemical, and material sciences. Herein, the authors report a deoxytrifluoromethylation/aromatization strategy that converts readily available cyclohexan(en)one substrate into highly substituted trifluoromethyl arenes. |
---|---|
ISSN: | 2041-1723 2041-1723 |
DOI: | 10.1038/s41467-024-52035-9 |