Photoredox-Mediated Minisci C-H Alkylation Reactions between N-Heteroarenes and Alkyl Iodides with Peroxyacetate as a Radical Relay Initiator.

We developed a protocol for photoredox-mediated Minisci C-H alkylation reactions of N-heteroarenes in which readily available tert-butyl peroxyacetate acts as a radical relay precursor to generate alkyl radicals from alkyl iodides. This mild protocol tolerated a broad range of functional groups and could therefore be used for late-stage functionalization of complex nitrogen-containing natural products and drugs. Remarkably, by adopting a polarity-reversal strategy, we accomplished reactions that brought together an electron-deficient radical, a heteroarene to add alkene by means of a three-component radical relay process.