A Dodecacationic Organic Cage for Visible-Light Multicomponent Reactions

Organic cages with large cavities that support multiguest encapsulation and photocatalysis provide environmentally benign, sustainable platforms for regulating reactivity and exploring new multicomponent reactions for potentially bioactive molecule screening in drug discovery, but their rational construction remains challenging. Here, we use a novel macrocycle-to-cage strategy to construct a dodecacationic organic cage with a large cavity, framed by four 1,3,5-triazine-2,4,6-tris(pyridin-1-ium) sites, which can encapsulate two phenolic guests. This encapsulation-based confinement mediates unprecedented visible-light-driven multicomponent reactions of two phenolic substrates with one olefin, affording difunctionalized products containing bioactive moieties. Therefore, we establish a rational strategy for constructing large organic hosts that integrate multiguest encapsulation with visible-light-mediated catalysis, enabling previously inaccessible multicomponent reaction pathways and providing a route to rapidly populate libraries of potentially bioactive molecules.