The C-B bonds generated by hydroboration are reactive with various reagents, the most common one being hydrogen peroxide. Because the addition of H-B to olefins is stereospecific, this oxidation reaction will be diastereoselective when the alkene is trisubstituted. Hydroboration-oxidation is thus an excellent way of producing alcohols in a stereospecific and anti-Markovnikov fashion.
Hydroboration can also lead to amines by treating the intermediate organoboranes with monochloramine or O-hydroxylaminesulfonic acid (HSA).
Terminal olefins are converted to the corresponding alkyl bromides and alkyl iodides by treating the organoborane intermediates with bromine or iodine. Such reactions have not however proven very popular, because succinimide based reagents such as NIS and NBS are more versatile and do not require rigorous conditions as do organoboranes.
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