A Dodecacationic Organic Cage for Visible-Light Multicomponent Reactions
Shuai Fang, Zhongwen Liu, Bohan Zhao, Mengbin Wang, Guangcheng Wu, Xueze Zhao, Mingrui Xiao, Zhi Chen, Han Han, Shang Li, Hongjie Luo, Sheng-Nan Lei, Ruihua Zhang, Chun Tang, Yi-Kang Xing, Yan-Fang Wang, Yiying Zhu, Hongliang Wang, Junling Sun, Charlotte L. Stern, Xiaopeng Li, Bin Hua, Jun Guo, Timothy R. Cook, J. Fraser Stoddart, Feihe HuangAbstract
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.