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...

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Veröffentlicht in:Organic letters 2021-11, Vol.23 (22), p.8810-8815
Hauptverfasser: Kim, Ha Eun, Choi, Jun-Ho, Chung, Won-jin
Format: Artikel
Sprache:eng
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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