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DOI: 10.1055/s-2006-949619
Benzophenone Imine
Publication History
Publication Date:
24 August 2006 (online)
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Introduction
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]
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.
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