Trifluoromethylchlorosulfonylation of alkenes: evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst.

Dattatraya B Bagal, Georgiy Kachkovskyi, Matthias Knorn, Thomas Rawner, Bhalchandra M Bhanage, Oliver Reiser

Angewandte Chemie (International ed. in English) 2015 Jun 8

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A visible-light-mediated procedure for the unprecedented trifluoromethylchlorosulfonylation of unactivated alkenes is presented. It uses [Cu(dap)2]Cl as catalyst, and contrasts with [Ru(bpy)3]Cl2, [Ir(ppy)2(dtbbpy)]PF6, or eosin Y that exclusively give rise to trifluoromethylchlorination of the same alkenes. It is assumed that [Cu(dap)2]Cl plays a dual role, that is, acting both as an electron transfer reagent as well as coordinating the reactants in the bond forming processes. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Dattatraya B Bagal, Georgiy Kachkovskyi, Matthias Knorn, Thomas Rawner, Bhalchandra M Bhanage, Oliver Reiser. Trifluoromethylchlorosulfonylation of alkenes: evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst. Angewandte Chemie (International ed. in English). 2015 Jun 8;54(24):6999-7002