American Chemical Society
Browse

Synthesis of Trifluoromethylated Sultones from Alkenols Using a Copper Photoredox Catalyst

Download (5.51 MB)
journal contribution
posted on 2016-06-21, 00:00 authored by Thomas 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.

History