Triphosgene/KF-mediated acyl fluoride synthesis <i>via in situ</i> fluoro(chloro)phosgene
The transformation of carboxylic acids into acyl fluorides <i>via</i> triphosgene-mediated deoxyfluorination utilizing inexpensive potassium fluoride (KF) has been achieved. This method affords a diverse range of acyl fluorides in high yields and exceptional purity. Analysis using <sup>19</sup>F NMR spectroscopy reveals that fluorophosgene and chlorofluorophosgene, generated <i>in situ</i>, serve as the reactive intermediates crucial to the conversion process. The protocol exhibits excellent functional group tolerance, enabling late-stage modification of biologically relevant compounds, and is scalable for both lab and industrial use. Acyl fluorides also proved valuable as precursors for amides, organic intermediates, and fluorine donors.
Authors
- Elsayed M. Mahmoud
- Wesam Saber Shehab (ORCID: https://orcid.org/0000-0002-5246-3491)
- Ibrahim M. Salem
- Mohammed Marzouk (ORCID: https://orcid.org/0000-0003-4853-2252)
- Tarek S. Ibrahim (ORCID: https://orcid.org/0000-0002-3049-4617)
- doaa atef elsayed (ORCID: https://orcid.org/0000-0001-8139-8548)
Institutions
- King Abdulaziz University (SA)
- Zagazig University (EG)
- Gifu University (JP)
- Sphinx University (EG)
- Al-Farahidi University
- Assiut University (EG)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00735f
- Citations
- 2
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 1.58