Visible-Light Mediated 1,2-Difunctionalization of Alkenes via Radical-Polar Crossover and Remote 1,5-Radical Translocation

We report the first external photocatalyst-free 1,2-difunctionalization of alkenes via radical-polar crossover pathway combined with remote 1,5-hydrogen atom transfer. In this strategy, indole derivatives play dual roles as nucleophilic reagents and photocatalysts. This approach demonstrates a broad substrate scope, with over 46 examples yielding products ranging from 46 to 94%. Mechanistic studies, including radical trapping experiments and Stern-Volmer quenching analyses, reveal a self-sustained photoredox cycle that operates without needing for an external photocatalyst.