Interlocking Pseudorotaxanes through Borane- and Boronic Ester-Mediated Carbon-Carbon Bond Formation.

Employing 9-BBN and pinacol boronic ester as surrogate stoppers, pseudorotaxanes presenting terminal alkenes can be transformed into organoborane or organoboronate rotaxanes, respectively. Various boron-based reactions can then be used to replace these temporary stoppers with bulky derivatives of aromatic bromides, α-bromo ketones, or 1-bromo-1-alkynes, facilitating the selective formation of sp3-sp2, sp3-sp3, and sp3-sp carbon-carbon single bonds, respectively.