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

Year 2021, Volume: 11 Issue: 3, 2102 - 2111, 01.09.2021

Adem Korkmaz

https://doi.org/10.21597/jist.845894

Cited By: 4

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

Supporting Institution

Muş Alparslan Üniversitesi

Project Number

BAP-17-TBMY-4901-01

Thanks

The author thanks Muş Alparslan University Research Foundation (grant no. BAP-17-TBMY-4901-01), which provides financial support for this study and the author also thanks Prof. Dr. Tahir Daşkapan (Dept. of Chemistry, Ankara Universty, Ankara) for helping to evaluate this work.

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