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Halogen-Bond-Promoted Photoactivation of Perfluoroalkyl Iodides: A Photochemical Protocol for Perfluoroalkylation Reactions

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journal contribution
posted on 06.03.2017, 00:00 by Yaxin Wang, Junhua Wang, Guo-Xing Li, Gang He, Gong Chen
A new protocol for photochemical perfluoroalkylation reactions using perfluoroalkyl iodide, amine additive, and THF solvent is reported. This protocol does not require a photoredox catalyst and proceeds at ambient temperature with irradiation from a compact fluorescent lamp, low-intensity UV lamp, or sunlight. This protocol can be applied to the synthesis of perfluoroalkyl-substituted phenanthridines as well as effect the iodo-perfluoroalkylation of alkenes/alkynes and the C–H perfluoroalkylation of electron-rich arenes and heteroarenes. This C–H perfluoroalkylation reaction offers a unique method for site-selective labeling of oligopeptides at the tryptophan residue.