Yinglu Wang, Weijie Zheng, Youkun Liu, Yong Li, Shipeng Luo, Changlong Zheng, Zixin Yang, Chenguang Liu, Hu Zhu
Despite the metabolic and geometric advantages of bicyclo[1.1.1]pentane (BCP), click-ready orthogonal BCP linkers remain limited. We report an azide-selenoxide bifunctional BCP linker via azido selenenylation of [1.1.1]propellane and oxidation, installing a benzyl selenoxide and an azide at opposite termini. The selenoxide enables benzyne trapping and interrupted Pummerer functionalization of phenols, including tyrosine-selective modification of oligopeptides, while the azide supports CuAAC, Staudinger ligation, and reductive acylation.