Aminoborohydrides. 12. Novel Tandem SNAr Amination−Reduction Reactions of 2-Halobenzonitriles with Lithium N,N-Dialkylaminoborohydrides
- 21 February 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (6) , 1999-2004
- https://doi.org/10.1021/jo001388j
Abstract
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.Keywords
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