Arylethylamines are abundant motifs in myriad natural products and pharmaceuticals, so efficient methods to synthesize them are valuable in drug discovery. Herein, we summarize the initial work from our group on alkene aminoarylation and detail its inherent limitations. We then describe two distinct approaches we have recently implemented to expand the alkene scope of the reaction and avert undesired side reactions. In both cases, we employ photoredox catalysis to generate electrophilic N-centered radicals adjacent to heteroatoms to form C-N bonds, then repurpose the heteroatom as a leaving group in a 1,4-aryl migration (Smiles-Truce rearrangement) to forge a C-C bond. Scope, mechanism, and persisting limitations are discussed.

Two-pronged evolution of N-centered radical aminoarylation <i>via</i> substrate or reagent redesign

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ACS Fall 2022

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Two-pronged evolution of N-centered radical aminoarylation via substrate or reagent redesign