The B/Sb Diagonal Relationship: Hydrostibination

A rigid naphthalenediamine framework has been used to prepare antimony hydrides that feature LUMO shapes and energies strikingly similar to those of secondary boranes. Exploiting this feature, we report the first example of uncatalyzed hydrostibination of robust CC double and triple bonds, as well as C=O, and N=N bonds as a new elementary hydrometallation reaction analogous to hydroboration. In the alkyne case, a Z-olefin is formed and in the reaction with N=N bonds, hydrostibination and hydrogenation are both observed. These results endorse the notion of a diagonal relationship between the lightest p-block element and the heaviest Group 15 elements and may lead to the realization of novel reaction chemistry.