Metal-free photochemical aromatic perfluoroalkylation of α-cyano arylacetates

Angew Chem Int Ed Engl. 2014 May 5;53(19):4921-5. doi: 10.1002/anie.201402008. Epub 2014 Mar 25.

Abstract

We report here an operationally simple protocol for the direct aromatic perfluoroalkylation and trifluoromethylation of α-cyano arylacetates. This metal-free approach, which occurs at ambient temperature and under visible-light irradiation, is driven by the photochemical activity of electron donor-acceptor (EDA) complexes, formed in situ by the interaction of transiently generated enolates and perfluoroalkyl iodides. Preliminary mechanistic studies are reported.

Keywords: CH functionalization; perfluoroalkylation; photochemistry; synthetic methods; trifluoromethylation.