Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation

Abstract

Despite the many recent advances in exploiting stoichiometric charge-transfer complexes in visible light promoted single-electron redox reactions, catalytic approaches to charge-transfer complex formation remain limited. This report describes the radical perfluoroalkylation of electron-rich (hetero)arenes and iodoperfluoroalkylation of alkenes and alkynes promoted by a substituted hydroquinone catalyst. Mechanistic and computational studies indicate that the reaction is initiated by the formation of a visible light absorbing halogen bonding complex between the hydroquinone catalyst and the perfluoroalkyl iodide radical precursor.

Radical Perfluoroalkylation Enabled by a Catalytically Generated Halogen Bonding Complex and Visible Light Irradiation

“…In this report, we present the radical perfluoroalkylation of electron-rich (hetero)arenes and the iodoperfluoroalkylation of alkenes and alkynes promoted by the visible light irradiation of a catalytically generated CTC between a HQ catalyst and the perfluoroalkyl halide radical precursor (Scheme 1). 15 Insight into the underlying mechanism of these transformations is also disclosed.…”