Direct Electrochemical Ritter-Type Amination of Electron-Deficient Arenes

Due to the high oxidation potentials of electron-deficient aromatic hydrocarbons, it is difficult to achieve the direct oxidative C(sp(2))-H bonds functionalizations of such substrates. Herein, we develop a Ritter-type amination of electron-deficient aromatics by merging electricity and sulfate. This practical and straightforward method provides a series of acetanilides from simple electron-deficient arenes, including mono-, di- and tri-substituted arenes (22 examples, up to 75 %) with moderate to good yields under mild conditions. This method is characterized by cheap and readily available regents, atom and step economy.

Automated summary

In this study, a practical and straightforward Ritter-type amination of electron-deficient aromatics was developed using electricity and sulfate. This method provides a series of acetanilides from simple electron-deficient arenes with moderate to good yields under mild conditions. It is characterized by cheap and readily available regents, atom and step economy.