Aryl C-N bond formation by electrophilic amination of diarylcadmium reagents with O-substituted ketoximes

DAŞKAPAN T., Korkmaz A.

SYNTHETIC COMMUNICATIONS, vol.46, no.9, pp.813-817, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 46 Issue: 9
  • Publication Date: 2016
  • Doi Number: 10.1080/00397911.2016.1177729
  • Journal Name: SYNTHETIC COMMUNICATIONS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.813-817
  • Keywords: Amination, amines, benzamides, copper catalysis, organocadmium, oximes, GRIGNARD-REAGENTS, PRIMARY AMINES, DIORGANOZINC REAGENTS, DERIVATIVES, METHYLHYDROXYLAMINE, SULFONYLOXIME, CADMATION
  • Ankara University Affiliated: Yes

Abstract

Diorganocadmium reagents cannot react with ketoxime at room temperature. 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 cannot help dialkyl-, dicycloalky-, and dibenzylcadmium reagents to react with ketoxime. Our Aryl C-N bond formation method does not include cadmium excretion into the environment.