Light-Promoted Radical Arylation of Nitrones with Triazenes
Vyacheslav I Supranovich1, Alexander D Dilman1
1N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
Abstract:
Application of aryltriazenes as safe precursors of aryl radicals for the direct hydroarylation of nitrones, furnishing substituted hydroxylamines, is described. The reaction proceeds under visible-light irradiation using sodium ascorbate as a reductant and acetic acid as a proton source. Light-induced E to Z isomerization of triazenes, which results in enhanced reactivity of the Z-isomer and eliminates the need for a photocatalyst, is a key feature of the method. The scope of the triazene component is limited to electron-rich and neutral aryls.
More Related Videos
Related Concept Videos
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Electrophilic Aromatic Substitution: Nitration of Benzene
Radical Reactivity: Nucleophilic Radicals
Preparation of Nitriles
Nitrosation of Enols


