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The first step of hydroboration–oxidation usually involves $\ce{BH3}$ accompanied by THF. Is it possible for hydroboration to occur without the presence of THF? Borane is incredibly reactive. Wouldn't it just react by itself without being stabilized by THF?

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Borane dimerises to diborane which does all the reactions of borane, including hydroborating alkenes. Diborane gas is commercially available if you wish to use it rather than stabilised borane, and have the equipment and skills to handle it. A number of other stabilisers are used for borane and are commercially available e.g. dimethyl sulfide, ammonia, triethylamine, pyridine.

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  • $\begingroup$ But practically speaking, you need a stabilizer without which the reaction will not take place? $\endgroup$
    – user28684
    Commented Dec 10, 2022 at 17:05
  • $\begingroup$ @user28684 Not so. If you use gaseous diborane the reaction will take place. $\endgroup$
    – Waylander
    Commented Dec 10, 2022 at 22:38

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