Catalytic Stereoselective Intermolecular Fluoroacylation of Unactivated Alkynes via C–F Bond Reconstruction
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.
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Authors: Tanmay Kanji, Asma A. Alharthi, Abdulrahman H. Husayni, Pippa Wainwright, Thomas Wirth, Rebecca L. Melen, Louis C. Morrill
Institutions: University of Jeddah, Cardiff University, University of Bath, Jazan University, AstraZeneca (Singapore), AstraZeneca (Poland)