Exploiting
charge-transfer complexes in visible light-promoted
single-electron redox reactions is a promising route for opening novel
synthetic pathways, and catalytic approaches to complex formation
are critical for facilitating this chemistry. This report describes
the use of a substituted hydroquinone catalyst to promote radical
perfluoroalkylation reactions. Mechanistic studies indicate that the
reaction is initiated through formation of a visible light-absorbing
halogen bonding complex between the hydroquinone catalyst and the
perfluoroalkyl halide radical precursor.
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.
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