Why is the borane–THF complex used for hydroboration?

1 Answer
Dec 1, 2014

Answer:

The borane-THF complex (BTHF) is used for hydroboration for reasons of safety and convenience.

Explanation:

The active ingredient is borane, #"BH"_3#, but borane is a highly toxic gas.

Borane exists naturally as the dimer #"B"_2"H"_6# (diborane), but diborane mixes easily with air and forms explosive mixtures.

Also, it ignites spontaneously in moist air at room temperature.

In a solution in THF, borane exists as a loose Lewis acid-base complex. This allows boron to have an octet and makes the reagent more stable.

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The solution is commercially available in a 1 mol/L concentration in volumes from 25 to 800 mL.

It is much more convenient to work with the solution than with a gas. Even so, the solution must be stored at 2 to 8 °C, and it must have a stabilizer added.

Borane forms a more stable and more soluble Lewis acid-base complex with dimethyl sulfide:

#"H"_3stackrelcolor(blue)("-")("B")"-"stackrelcolor(blue)(+)("S")("CH"_3)_2#

It is available in concentrations of 2, 5, and 10 mol/L and in volumes from 25 mL to 18 L.

That should make it a more convenient reagent than the BTHF complex.

There is only one problem: It has the highly disagreeable smell of rotten cabbage!