In the hydroboration reactions of alkenes I've seen so far, they were always followed by oxidation with $\ce{H2O2/NaOH}$ (to yield alcohols).

Today I found a peculiar reaction in which acetic acid-d1 was added after hydroboration to give a deuterated product:

Formation of (1R,2R)-1-methylcyclohexane-2-d from 1-methylcyclohex-1-ene

I don't quite understand what exactly happens after the hydroboration part. Can someone enlighten me here?

up vote 10 down vote accepted

Acetic acid effects protonolysis of the borane:

Mechanism for borane protonolysis

If AcOD is used then RD (instead of RH) is formed.

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