Related Experiment Video
Updated: Apr 25, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Room-temperature Cu(II)-catalyzed chemo- and regioselective ortho-nitration of arenes via C-H functionalization
Pradeep Sadhu1, Santhosh Kumar Alla, Tharmalingam Punniyamurthy
1Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.
Abstract:
An efficient Cu-catalyzed chemo- and regioselective ortho-nitration of N,1-diaryl-5-aminotetrazoles and N,4-diaryl-3-amino-1,2,4-triazoles has been described with good functional group compatibility. The procedure features the use of an operationally simple protocol utilizing the commercially available less toxic CuCl2·2H2O as catalyst and Fe(NO3)3·9H2O as nitration source at room temperature. Removal of the 5-aminotetrazole directing group has been demonstrated using base hydrolysis to afford substituted 2-nitroanilines.
Related Concept Videos
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Electrophilic Aromatic Substitution: Nitration of Benzene
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Overview
The nitrous acid is unstable. Hence, it is formed in situ from a solution of sodium nitrite and cold aqueous acids such as hydrochloric or sulfuric acid. In an acidic solution, the –OH group of nitrous acid undergoes protonation to give oxonium ion, followed by...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

