Angew. Chem. Int. ed. (2023) by BSM

Regio- and Stereoselective Hydroelementation of SF5-Alkynes and Further Functionalizations.
Lucas Popek, Dr. Jorge Juan Cabrera-Trujillo, Dr. Vincent Debrauwer, Dr. Nicolas Blanchard, Dr. Karinne Miqueu, Dr. Vincent Bizet
Angew. chem. Int. Ed., 202361, e202300685


Herein is described a fully regio- and stereoselective hydroelementation reaction of SF5-alkynes with N, O and S-nucleophiles and further functionalization of the corresponding Z-(hetero)vinyl-SF5 intermediates, a suitable platform to access α-SF5 ketones and esters, β-SF5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF5- and CF3-alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.