Electrochemically Driven Denitrative Cyanation of Nitroarenes
Yiyi Chen1, Qisheng Chen1, Shuangquan Zhang1
1School of Chemical Engineering and Materials, Changzhou Institute of Technology, No. 666 Liaohe Road, Changzhou 213032, China.
Abstract:
A practical denitrative cyanation of feedstock nitroarenes under mild and transition metal-free reaction conditions has been developed. The key to success lies in the use of electrochemically driven, inexpensive ionic liquid N-methylimidazolium p-toluenesulfonate-promoted selective cathode reduction of nitroarenes to anilines, followed by diazoation, cathode reduction to form the aryl radical, and the essential radical cyanation process in one pot. Our protocol shows broad functional group tolerance and can be applied for the modification of bioactive targets.
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
Preparation of Nitriles
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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...
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...


