Rapid Access to Fluorinated Anilides via DAST-Mediated Deoxyfluorination of Arylhydroxylamines

A new strategy for the synthesis of fluorinated anilides in the absence of metals and oxidants has been developed. This deoxyfluorination of N-arylhydroxylamines with diethylaminosulfur trifluoride (DAST) proceeded smoothly under mild conditions, and the ortho- or para-fluorinated aromatic amine pro...

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Veröffentlicht in:Organic letters 2021-12, Vol.23 (23), p.9332-9336
Hauptverfasser: Zhang, Zhuyong, Luo, Junfei, Gao, Hongyin
Format: Artikel
Sprache:eng
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Zusammenfassung:A new strategy for the synthesis of fluorinated anilides in the absence of metals and oxidants has been developed. This deoxyfluorination of N-arylhydroxylamines with diethylaminosulfur trifluoride (DAST) proceeded smoothly under mild conditions, and the ortho- or para-fluorinated aromatic amine products were prepared in moderate to good yields. Structurally diverse fluorinated anilides, including heterocyclic and pharmaceutically relevant molecules, can be efficiently constructed by this protocol.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c03779