DOI: 10.1021/acs.orglett.6c03620 ISSN: 1523-7060
Catalytic Stereoselective Intermolecular Fluoroacylation of Unactivated Alkynes via C–F Bond Reconstruction
Tanmay Kanji, Asma A. Alharthi, Abdulrahman H. Husayni, Pippa Wainwright, Thomas Wirth, Rebecca L. Melen, Louis C. MorrillAbstract
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.