Aminoborohydrides. 12. Novel tandem S(N)Ar amination-reduction reactions of 2-halobenzonitriles with lithium N,N-dialkylaminoborohydrides.
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 S(N)Ar 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.
Thomas
S
S
Department of Chemistry and Biochemistry, University of California at Santa Cruz, Santa Cruz, California 95064, USA.
Collins
C J
CJ
Cuzens
J R
JR
Spiciarich
D
D
Goralski
C T
CT
Singaram
B
B