C-N, C-O and C-S Ullmann-Type Coupling Reactions of Arenediazonium <i>o</i>-Benzenedisulfonimides

Abstract

Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Cu(I) catalysed Ullmann-type coupling. The synthetic protocols are mild and easy, and produced either N-alkylanilines, aryl ethers, or thioethers in fairly good yields (18 positive examples, average yield 66%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further reactions. It is noteworthy that diazonium salts have been used as electrophilic partners in the Ullmann-type protocol for the first time.

Keywords

• Ullmann-type coupling
• copper catalysis
• arenediazonium salts