Synthesis of Trifluoromethylated Sultones from Alkenols Using a Copper Photoredox Catalyst.

A photo-redox-catalyzed procedure for the one-step formation of sultones from α,ω-alkenols and trifluoromethylsulfonyl chloride is described. Using [Cu(dap)2]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)3]Cl2 or fac-Ir(ppy)3 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.

Citation

Thomas Rawner, Matthias Knorn, Eugen Lutsker, Asik Hossain, Oliver Reiser. Synthesis of Trifluoromethylated Sultones from Alkenols Using a Copper Photoredox Catalyst. The Journal of organic chemistry. 2016 Jul 6

PMID: 27327532

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