Catalytic stereoselective intermolecular fluoroacylation of unactivated alkynes via C–F bond reconstruction

Kanji, Tanmay ORCID: https://orcid.org/0000-0001-6426-5014, Alharthi, Asma A., Husayni, Abdulrahman H., Wainwright, Pippa, Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667, Melen, Rebecca L. ORCID: https://orcid.org/0000-0003-3142-2831 and Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 2026. Catalytic stereoselective intermolecular fluoroacylation of unactivated alkynes via C–F bond reconstruction. Organic Letters 10.1021/acs.orglett.6c03620

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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.

Item Type:	Article
Date Type:	Published Online
Status:	In Press
Schools:	Schools > Chemistry Schools > Physical, Chemical & Environmental Sciences
Publisher:	American Chemical Society
ISSN:	1523-7060
Date of First Compliant Deposit:	6 October 2026
Date of Acceptance:	21 September 2026
Last Modified:	06 Oct 2026 13:45
URI:	https://orca.cardiff.ac.uk/id/eprint/190040

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