Regio- and Stereoselective Hydroelementation of SF5-Alkynes and Further Functionalizations.

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 alpha-SF5 ketones and esters, beta-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.

Automated summary

This article describes a fully regio- and stereoselective hydroelementation reaction of SF5-alkynes with N, O, and S-nucleophiles, and the further functionalization of the resulting Z-(hetero)vinyl-SF5 intermediates. This reaction provides a suitable platform for accessing alpha-SF5 ketones and esters, as well as beta-SF5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF5- and CF3-alkynes have been conducted to highlight and explain the observed differences in reactivity and selectivity between these two fluorinated motifs.