Aminoborohydrides. 12. Novel Tandem SNAr Amination-reduction Reactions of 2-Halobenzonitriles with Lithium N, N-Dialkylaminoborohydrides

…, D Spiciarich, CT Goralski, B Singaram

Index: Thomas; Collins; Cuzens; Spiciarich; Goralski; Singaram Journal of Organic Chemistry, 2001 , vol. 66, # 6 p. 1999 - 2004

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Citation Number: 32

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. ...