this work describes the preparation of new shelf-stable aziridinyldifluoroborates even in enantioenriched form that can serve either as Suzuki–Miyaura reagents and as new bifunctional Lewis pairs potentially useful as catalysts or tweezers for small-molecule binding. Such thus far undescribed aziridinedifluoroborates, which can be used for the ortho-functionalization of aromatic aziridines, are, to the best of our knowledge, the first examples of aziridine-functionalized cross-coupling reagents. The methodology could be expanded to other benzylamine derivatives and aryl-substituted N-heterocycles in order to obtain new shelf-stable organoboron reagents. More work is underway in our laboratory in order to expand the synthetic utility of these new reagents.