posted on 2016-06-21, 00:00authored byThomas Rawner, Matthias Knorn, Eugen Lutsker, Asik Hossain, Oliver Reiser
A photo-redox-catalyzed
procedure for the one-step formation of
sultones from α,ω-alkenols and trifluoromethylsulfonyl
chloride is described. Using [Cu(dap)<sub>2</sub>]Cl (1 mol %), a
wide range of substrates can be cleanly converted to the target compounds,
while commonly employed photoelectron transfer catalysts such as [Ru(bpy)<sub>3</sub>]Cl<sub>2</sub> or <i>fac</i>-Ir(ppy)<sub>3</sub> fail in this transformation. The obtained fluorinated sultones are
attractive as potential electrolyte additives or as structural motifs
in drug synthesis, with the latter being demonstrated with the synthesis
of a trifluoroethyl-substituted analogue of a benzoxathiin that has
high anti-arrhythmic activity.