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.