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.
Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
Thomas
T
Rawner
Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
Matthias
M
Knorn
Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
Eugen
E
Lutsker
Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
Asik
A
Hossain
Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
Oliver
O
Reiser
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D009282:Naphthalenesulfonates / Q000138:chemical synthesis*; D055668:Photochemical Processes
D000475:Alkenes; D006845:Hydrocarbons, Fluorinated; D009282:Naphthalenesulfonates; D003300:Copper; C016768:naphthosultone