Photoredox 1,2-Alkylarylation of Alkenes with 1-(Allyloxy)-2-iodobenzenes and Cyano(hetero)aromatics Involving XAT-Enabled Annulation

A visible-light-induced three-component photoredox 1,2-alkylarylation of alkenes with 1-(allyloxy)-2-iodobenzenes and cyano(hetero)aromatics for the synthesis of functionalized 2,3-dihydrobenzofurans is developed. The reaction employs 1-(allyloxy)-2-iodobenzenes as the alkyl radical resources via aminoalkyl radical-initiated halogen atom transfer (XAT) and intramolecular aryl radical addition across the alkene moiety. The resulting alkyl radicals then execute sequential intermolecular radical addition across the alkenes, followed by radical-radical coupling with a wide range of cyano(hetero)aromatics, achieving efficient 1,2-alkylarylation of alkenes featuring excellent selectivity control, broad functional group tolerance, operational sustainability, and versatility.