I want the following conversion to take place$$\ce{Ph-R-CH2-BH2 -> Ph-R-CH3}$$ Does acetic acid react with the given alkyl borane to get this alkane? If yes, what is the correct mechanism? Please explain the mechanism in detail.
I am a newbie to organic chemistry mechanisms(spent 3 weeks,hard work)and I have studied quite a bit of acid-base reactions,electrophilic and nucleophlic substitutions; but cant make this one out.
I have a tried a reaction similar to oxidation and hydrolysis of alkylboranes using hydrogen peroxide (refer to this):
There we have an $\ce{H-O-O-}$ ion,and after it gets attached to the boron by donating an electron pair to form a $\ce{Ph-R-B^{-}-H2-O-O-H}$, thereafter Boron donates a proton to the Oxygen atom attached to it and simultaneously the $\ce{-OH}$ group leaves.That is how the mechanism proceeds in that case.
But here,the problem is in the ion $\ce{CH3COO-}$;
even if the boron donates a proton to the bonded $\ce{O}$ atom,$\ce{CH3C^{+}=O}$ is a VERY bad leaving group, hence it wont be correct. I tried thinking about a simple electrophilic substitution, but couldn't understand the nature of $\ce{BH2+}$ as a leaving group.
Any correct way in which acetic acid reacts?
