4.7 Article

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

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 3, Pages 3059-3064

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02598

Keywords

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Funding

  1. Natural Science Foundation of Shanghai [17ZR1429900]
  2. Chemical Engineering and Technology (Perfume and Aroma Technology) of Shanghai Plateau Discipline
  3. Shanghai Institute of Technology [ZQ2019-15]
  4. Opening Fund of Shanghai Key Laboratory of Chemical Biology

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This study presents a novel synthesis method involving cyanide ion-promoted nucleophilic displacement without transition metal catalysts to create nitrile-containing naphthalimide aryl ether derivatives, offering a new pathway for the preparation of diaryl ether derivatives.
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 diary! ether derivatives.

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