Homologative 1,3‐Functionalization of Alkenes via an Iodomethyl Thianthrenium Reagent

Despite tremendous progress in alkene 1,2-difunctionalization, analogous methods to generate 1,3-patterns from alkenes remain limited. Recently, Silvi and co-workers reported a homologative strategy to transform alkenes into 1,3-dielectrophiles (DOI: https://doi.org/10.1002/anov.70005). They introduce a novel iodomethyl thianthrenium salt as a precursor to methyl thianthrenium radical, which adds across unactivated alkenes. Substitution of the 1,3-dielectrophiles delivers a general homologative alkene difunctionalization platform.