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

Institutions

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
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Triphosgene/KF-mediated acyl fluoride synthesis via in situ fluoro(chloro)phosgene

Elsayed M. Mahmoud, Wesam Saber Shehab, Ibrahim M. Salem, Mohammed Marzouk et al.
2 citations
Organic & Biomolecular Chemistry
Fluorine in Organic Chemistry
1.58
article

Triphosgene/KF-mediated acyl fluoride synthesis via in situ fluoro(chloro)phosgene

Elsayed M. Mahmoud, Wesam Saber Shehab, Ibrahim M. Salem, Mohammed Marzouk, Tarek S. Ibrahim, doaa atef elsayed
article en
2 citations

Abstract

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.

Organic & Biomolecular ChemistryVol. 23(25)
King Abdulaziz University (SA), Zagazig University (EG), Gifu University (JP), Sphinx University (EG), Al-Farahidi University, Assiut University (EG)
Clean water and sanitation
Openalex Percentile: Top 17%
Fluorine in Organic Chemistry
1.58
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.