Does 9-BBN not act on internal alkynes or alkenes?

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SUMMARY

9-BBN (9-borabicyclo[3.3.1]nonane) is indeed more regioselective than borane-THF, making it a preferred choice for hydroboration reactions. While it can react with internal alkenes, the reaction rate is slower compared to terminal alkenes due to steric hindrance. The large substituents on 9-BBN are designed to promote boron addition at less sterically hindered sites, enhancing regioselectivity. Additionally, 9-BBN is available in solid form, providing a practical advantage over gaseous B2H6.

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Organic Chemistry question! Is 9-BBN too sterically hindered to even react with internal alkynes or alkenes? (to do hydroboration)
 
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I've seen claims that 9-BBN can react with internal alkenes, but I haven't attempted it myself. I imagine the reaction would take longer than a reaction with a terminal alkene. The goal of the big substituents is to favor boron addition at less sterically hindered sites with high regioselectivity. 9-BBN generally tends to be more regioselective than something like borane-THF. You can also get it in solid form, which is easier to use than gaseous B2H6.
 
Thanks!
 

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