Synthesis of α‑Ketoimidoyl Fluorides via Geminal Fluorine-Promoted Azide Rearrangement
Despite the promising synthetic potential, the utilization of imidoyl fluorides has been hampered by the lack of broadly applicable preparative methods. Herein, bench-stable α-ketoimidoyl fluorides were synthesized from geminal chlorofluorides through tandem azidation/rearrangement under mild condit...
Gespeichert in:
Veröffentlicht in: | Organic letters 2021-11, Vol.23 (22), p.8810-8815 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
Zusammenfassung: | Despite the promising synthetic potential, the utilization of imidoyl fluorides has been hampered by the lack of broadly applicable preparative methods. Herein, bench-stable α-ketoimidoyl fluorides were synthesized from geminal chlorofluorides through tandem azidation/rearrangement under mild conditions. The efficiency was consistently high, regardless of the steric and electronic environments. The synthetic utility of the α-ketoimidoyl fluoride was also demonstrated. Furthermore, the remarkable accelerating effect of the geminal fluorine substituent was identified and rationalized by density functional theory calculation. |
---|---|
ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.1c03309 |