72752-53-5Relevant articles and documents
Aminoborohydrides. 12. Novel tandem SNAr amination-reduction reactions of 2-halobenzonitriles with lithium N,N-dialkylaminoborohydrides
Thomas,Collins,Cuzens,Spiciarich,Goralski,Singaram
, p. 1999 - 2004 (2007/10/03)
A novel tandem amination-reduction reaction has been developed in which 2-(N,N-dialkylamino)benzylamines are generated from 2-halobenzonitriles and lithium N,N-dialkylaminoborohydride (LAB) reagents. These reactions are believed to occur through a tandem SNAr amination-reduction mechanism wherein the LAB reagent promotes halide displacement by the N,N-dialkylamino group, and the nitrile is subsequently reduced. This one-pot procedure is complimentary to existing synthetic methods and is an attractive synthetic tool for the nucleophilic aromatic substitution of halobenzenes with less nucleophilic amines. The (N,N-dialkylamino)benzylamine products of this reaction are easily isolated after a simple aqueous workup procedure in very good to excellent yields.