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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.