Introduction
<P>Benzophenone imine or (diphenylmethylene)amine (DPMA-H,
1 ) is a valuable reagent in organic synthesis.
[
1 ]
It is a commercially available liquid which is easily prepared by addition of phenylmagnesium
bromide to benzonitrile followed by hydrolysis with methanol
[
2 ]
or by reaction of benzophenone with ammonia.
[
3 ]
</P>
<P>Synthetic applications of
1 have been historically related to peptide chemistry, specifically as protecting group
of primary amines during the preparation of optically active α-amino acids.
[
4 ]
Used in conjunction with other anion-stabilising groups,
1 provides activation for proton abstraction. More recently, the development of highly
efficient tin-free palladium-catalysed amination methodologies by the groups of Buchwald
[
5 ]
and Hartwig
[
6 ]
increased its synthetic utility as convenient ammonia surrogate in catalysed coupling
reactions.</P>
