Related Experiment Video
Updated: Jun 4, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Copper-catalyzed oxidative cross-coupling of N,N-dimethylanilines with heteroarenes under molecular oxygen
Lehao Huang1, Tianmin Niu, Jun Wu
1Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Abstract:
Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparation. In this paper, we report a direct cross-coupling reaction of heteroarenes with N,N-dimethylanilines in the presence of copper catalyst. Oxygen and/or air are successfully used as the oxidant, which is of great importance to the industrialized economies. The reaction is compatible with a wide range of heterocycles, including indolizines, imidazoles, indoles, and aniline, to enable the formation of various alkylated heteroarenes under very mild reaction conditions.
Related Concept Videos
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Oxymercuration-Reduction of Alkenes
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

