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Comparison of Various Hydrogenation Methods

Reduction with Borane

Functional groups are listed in ascending order of reducibility.

Tab.1
Overview of the reduction of organic functional groups with borane
EductProductReduction
Fig.
Acyl chloride
inert
Fig.
Ester
Fig.
Alcohol
very difficult
Fig.
Nitrile
Fig.
Amine
Fig.
Ketone
Fig.
sec-Alcohol
Fig.
Alkene
Fig.
Alkyl borane
Fig.
Carboxylic acid
Fig.
Alcohol
facile

A comparison of these data with those for the reduction with LiAlH4 indicates that compounds which are easily reduced with borane are difficult to reduce with lithium aluminum hydride and vice versa.

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