Expanded Access to Fluoroformamidines via a Modular Synthetic Pathway

Fluoroformamidines are an underutilized and understudied functional group despite combining two of the most highly prized elements in drug design: nitrogen and fluorine. We report a practical and modular synthesis of fluoroformamidines via the rearrangement of in situ-generated amidoximes. High yiel...

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Bibliographic Details
Published inOrganic letters Vol. 26; no. 6; pp. 1277 - 1281
Main Authors Vogel, James A., Miller, Kirya F., Shin, Eunjeong, Krussman, Jenna M., Melvin, Patrick R.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.02.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
DEOXYFLUORINATION
FLUORINE
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Summary:Fluoroformamidines are an underutilized and understudied functional group despite combining two of the most highly prized elements in drug design: nitrogen and fluorine. We report a practical and modular synthesis of fluoroformamidines via the rearrangement of in situ-generated amidoximes. High yields in just 60 s at room temperature highlight the efficiency of this protocol. Furthermore, fluoroformamidines proved to be useful intermediates in the synthesis of diverse ureas and carbamimidates.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00131