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

17 November 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


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.


Halogen Bonding
Electron Donor-Acceptor Complex

Supplementary materials

Supporting Information
Experimental procedures, reaction optimization, compound charac-terization, computational studies and NMR spectra.


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