Metal-Free Photochemical Aromatic Perfluoroalkylation of α-Cyano Arylacetates


  • Research support from the Institute of Chemical Research of Catalonia (ICIQ) Foundation and the European Research Council (ERC Starting Grant n. 278541—ORGA-NAUT to P.M.) is gratefully acknowledged. M.N. and G.B. are grateful to the MEC for FPU fellowships (refs. AP2010-1963 and AP2009-0950)


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.