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Peer-reviewedCC BYOrganic letters

Catalytic Stereoselective Intermolecular Fluoroacylation of Unactivated Alkynes via C-F Bond Reconstruction.

  • Tanmay Kanji1
  • Asma A Alharthi2,3
  • Abdulrahman H Husayni2,4
  • Pippa Wainwright5
  • Thomas Wirth2
  • Rebecca L Melen1
  • Louis C Morrill6
6 affiliations
  1. 1Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, CardiffCF24 4HQ, United Kingdom.
  2. 2School of Chemistry, Cardiff University, Main Building, Park Place, CardiffCF10 3AT, United Kingdom.
  3. 3Department of Chemistry, College of Science, University of Jeddah, Jeddah21589, Kingdom of Saudi Arabia.
  4. 4Department of Physical Sciences, Chemistry Division, College of Science, Jazan University, Jizan45142, Kingdom of Saudi Arabia.
  5. 5Chemical Development, Pharmaceutical Technology & Development, Operations, AstraZeneca, MacclesfieldSK10 2NA, United Kingdom.
  6. 6Department of Chemistry, University of Bath, Claverton Down, BathBA2 7AY, United Kingdom.
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Abstract

Herein, we report a transition metal-free synthesis of monofluoroalkenes via a C-F bond reconstruction approach. The process employs inexpensive BF3·Et2O as a catalyst for the stereoselective intermolecular fluoroacylation of unactivated alkynes with alkyl/aryl acid fluorides to access various monofluoroalkene products (24 examples, typically >98:<2 Z:E). The synthetic utility of the products was demonstrated via their conversion into various heterocycles (pyrazoles, isoxazoles, and pyrimidines) and fluoroalkene-containing esters/amides.

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Cite

BibTeXRIS
BibTeX
@article{kanji2026catalytic,
  title = {{Catalytic Stereoselective Intermolecular Fluoroacylation of Unactivated Alkynes via C-F Bond Reconstruction.}},
  author = {Tanmay Kanji and Asma A Alharthi and Abdulrahman H Husayni and Pippa Wainwright and Thomas Wirth and Rebecca L Melen and Louis C Morrill},
  journal = {Organic letters},
  year = {2026},
  month = oct,
  doi = {10.1021/acs.orglett.6c03620},
  url = {https://europepmc.org/article/MED/42912214},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Catalytic Stereoselective Intermolecular Fluoroacylation of Unactivated Alkynes via C-F Bond Reconstruction.
AU  - Tanmay Kanji
AU  - Asma A Alharthi
AU  - Abdulrahman H Husayni
AU  - Pippa Wainwright
AU  - Thomas Wirth
AU  - Rebecca L Melen
AU  - Louis C Morrill
PY  - 2026
DA  - 2026/10/01
JO  - Organic letters
DO  - 10.1021/acs.orglett.6c03620
UR  - https://europepmc.org/article/MED/42912214
AB  - Herein, we report a transition metal-free synthesis of monofluoroalkenes via a C-F bond reconstruction approach. The process employs inexpensive BF3·Et2O as a catalyst for the stereoselective intermolecular fluoroacylation of unactivated alkynes with alkyl/aryl acid fluorides to access various monofluoroalkene products (24 examples, typically >98:<2 Z:E). The synthetic utility of the products was demonstrated via their conversion into various heterocycles (pyrazoles, isoxazoles, and pyrimidines) and fluoroalkene-containing esters/amides.
SN  - 1523-7060
SN  - 1523-7052
ER  -