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Ye, Ke-Yin; Song, Zhidong; Sauer, Gregory S.; Harenberg, Johannes H.; Fu, Niankai; Lin, Song (2018): Synthesis of Chlorotrifluoromethylated Pyrrolidines by Electrocatalytic Radical Ene-Yne Cyclization. In: Chemistry-A European Journal, Vol. 24, No. 47: pp. 12274-12279
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Abstract

The stereoselective synthesis of chlorotrifluoromethylated pyrrolidines was achieved using anodically coupled electrolysis, an electrochemical process that combines two parallel oxidative events in a convergent and productive manner. The bench-stable and commercially available solids CF3SO2Na and MgCl2 were used as the functional group sources to generate CF3. and Cl-., respectively, via electrochemical oxidation, and the subsequent reaction of these radicals with the 1,6-enyne substrate was controlled with an earth-abundant Mn catalyst. In particular, the introduction of a chelating ligand allowed for the ene-yne cyclization to take place with high stereochemical control over the geometry of the alkene group in the pyrrolidine product.