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Organic Letters· 2026Q1

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

Tanmay Kanji, Asma A. Alharthi, Abdulrahman H. Husayni, Pippa Wainwright et al.

Short summary

A new transition metal-free method synthesizes monofluoroalkenes from unactivated alkynes and acid fluorides using BF3·Et2O as a catalyst, achieving high stereoselectivity (>98:2 Z:E).

AI-generated from the title and abstract; the full text is not read.

Key points

  • Developed a transition metal-free catalytic method for fluoroacylation of unactivated alkynes.
  • Employs inexpensive BF3·Et2O as the catalyst.
  • Achieves high stereoselectivity, yielding Z-isomers in >98:2 ratio.
  • Demonstrated synthetic utility by converting products into heterocycles and esters/amides.

AI-generated from the title and abstract; the full text is not read.

Abstract

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.

The authors' abstract, as published at the source. Organic Letters, 2026 · DOI ↗

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Field: Pharmaceutical Science

Pharmaceutical SciencePharmacology, Toxicology and Pharmaceutics