Aryl C-N Bond Formation by Electrophilic Amination of Diarylcadmium Reagents with O -Substituted Ketoximes

CuCN catalysis allows diarylcadmium reagents to react with ketoxime and to give corresponding arylamines in good to high yields at room temperature. According to the electronic effects of the substituent attached to the aromatic ring, functionalized diarylcadmium reagents show meta-para selectivity in their amination reactions.

Also compared to diarylzinc reagents, diarylcadmium reagents react with O -substituted ketoxime under milder reaction conditions and they form corresponding arylamines in higher yields. CuCN, can not help dialkyl-, dicycloalky- and dibenzylcadmium reagents to react with ketoxime. Our Aryl C-N bond formation method we give here does not include cadmium excretion into the environment.