Cyanide Ion-Promoted Nucleophilic Displacement of Aromatic Nitro Groups: A Mild, One-Pot, Transition Metal-Free Synthesis of Nitrile-Containing Naphthalimide Aryl Ether Derivatives

J Org Chem. 2021 Feb 5;86(3):3059-3064. doi: 10.1021/acs.joc.0c02598. Epub 2021 Jan 12.

Abstract

Herein we report the novel synthesis of nitrile-containing naphthalimide aryl ether derivatives via transition metal-free cyanide ion-promoted nucleophilic displacement of nitronaphthalimide with alcohols or phenols. The transformation involves a one-pot reaction, which is operationally simple and mild and bereft of transition metal catalysts. This work provides a novel route for the preparation of diaryl ether derivatives.