Iodine-Photoredox Dual Catalysis Unlock Bifunctional Reactivity of α-Diazoesters in Radical Cascade Cyclization Reaction via Remote C–I Bond Dissociation

Abstract

Current radical cascade cyclization reactions involving α-diazoesters mainly rely on photo-driven proton-coupled electron transfer (PCET) path. In contrast, iodine-photoredox dual catalyzed radical cascade cyclization of α-diazoesters remain unexplored. In this work, we report the first divergent cycloaddition strategy that employs diazo compounds as C1 building blocks for the construction of fused five-membered rings under iodine-photoredox dual catalysis. Differing from prior PCET strategy, this approach unlocks the bifunctional reactivity of α-diazoesters, enabling them to serve both as radical precursors and radical trappers in radical cascade cyclization processes, providing a new mode of radical cascade cyclization of α-diazoesters by visible light-catalyzed.