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Updated: Jan 16, 2026

Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
Visible-Light-Induced [2π+2σ] Cycloaddition Enabled by Cage-Confined Photocatalysis for Precise Bicyclo[2.1.1]Hexane
Yanke Hao1, Jie Chen1, Zhiwei Jiao1
1MOE Laboratory of Bioinorganic and Synthetic Chemistry, GBRCE for Functional Molecular Engineering, LIFM, IGCME, School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, China.
None:
We disclose a visible-light-induced, diastereoselective [2π+2σ] photocycloaddition between readily available chalcones and 1,3-disubstituted bicyclo[1.1.0]butanes (BCBs) promoted by photoactive metal-organic cage (PMOC). This confined supramolecular catalysis method enables efficient synthesis of pharmaceutically relevant bicyclo[2.1.1]hexane (BCH) bioisosteres with remarkable atom economy and excellent diastereoselectivities, necessitating only 0.1 mol% catalyst loading. The success of this organic transformation arises from the synergistic action of the PMOC as a nanoreactor to combine selective substrate preorganization through host-guest interactions, efficient Ru(II)-mediated triplet energy transfer, and nano-spatial confinement effect that precisely control [2π+2σ] cyclization geometry while preventing competitive homodimerization.
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