Copper-Catalyzed Electrophilic Amination of Diarylcadmium Reagents Utilizing Acetone O-(4- chlorophenylsulphonyl)oxime and Acetone O-(2-naphthylsulphonyl)oxime as Amination Agent

Abstract

In this study, a CuCN catalyzed process of the diarylcadmium compounds by electrophilic amination method was developed using novel acetone O-(4-chlorophenylsulfonyl)oxime and acetone O-(2-naphthylsulfonyl)oxime. Herein, it has been demonstrated that primary arylamines can easily be obtained with good yields at room temperature by CuCN catalyzed amination of diarylcadmium reagents. It was settled down that the yield of primary arylamines depended strongly on the steric and electronic effects of organocadmium reagent and amination agent. In both amination reagents, meta-substituted arylamines were obtained in higher yields than para-substituted aryl amines. All reactions involving organocadmiums were carried out under an argon atmosphere by standard syringe/cannula methods. Amines as reaction products were separated from the reaction mixture as benzamide derivatives and purified and melting points, 1H NMR analysis determined their accuracy.

Keywords

• Electrophilic amination
• diarylcadmium reagents
• benzamides
• ketoximes
• copper catalysis
• copper catalysis

Project Number

BAP-17-TBMY-4901-01

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