Effect of fluorine or oxygen atom(s) in propargylic position on the reactivity in click chemistry

The use of especially designed ω-diynes allows to establish, through competitive reactions, the effect of C-F, C-OH, CF2, CO and C(OMe)2 substituents on the reactivity of neighbouring triple bonds in click chemistry and this gives not only a reactivity scale but also a direct access to the difference in activation energies between the competitive reaction pathways.

Graphical abstractNewly designed ω-diynes allow to establish, through competitive reactions, the effect of C-F, C-OH, CF2, CO and C(OMe)2 substituents on the reactivity of neighbouring triple bonds in click chemistry.Download full-size image