Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C−N Bond Cleavage

Muhammad Aliyu Idris, Kwang Ho Song, Sunwoo Lee

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Amides, such as N-benzoylsaccharin, N,N-diBocbenzamide, and N-phenyl-N-tosylbenzamides reacted with Et3N⋅3HF to provide the corresponding acyl fluorides in good yields. The reaction was conducted under environmentally friendly conditions using i-PrOAc as the solvent. Moreover, the reaction was performed at room temperature and did not require a transition-metal catalyst or additives. The methodology showed functional group tolerance toward amines, alkoxy, halides, ketones, esters, and aldehydes. (Figure presented.).

Original languageEnglish
Pages (from-to)2449-2453
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume364
Issue number14
DOIs
Publication statusPublished - 2022 Jul 19

Bibliographical note

Funding Information:
This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF-2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center.

Funding Information:
. This research was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean government (MSIT) (NRF‐2021R1 A2 C1005169). Spectral and HRMS data were obtained at the Korea Basic Science Institute, Gwangju center and Daegu center

Publisher Copyright:
© 2022 Wiley-VCH GmbH.

Keywords

  • C−N Bond Cleavage
  • N-benzoylsaccharin
  • acyl fluorides
  • amides
  • fluorides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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