Chemical Research in Chinese Universities ›› 2009, Vol. 25 ›› Issue (5): 638-643.

• Articles • Previous Articles     Next Articles

Ce(SO4)2-mediated Oxidative Coupling of Primary Aromatic Amines in Water

LU Wen-chao and XI Chan-juan*   

  1. Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Ministry of Education, Department of Chemistry, Tsinghua University, Beijing 100084, P. R. China
  • Received:2008-09-26 Revised:2008-10-16 Online:2009-09-25 Published:2009-12-07
  • Contact: XI Chan-juan. E-mail: cjxi@tsinghua.edu.cn
  • Supported by:

    Supported by the National Natural Science Foundation of China(No.20572058).

Abstract:

The oxidative coupling of primary aromatic amines was investigated. Ce(SO4)2 can mediate the oxidative coupling of primary aromatic amines in water to dimers, trimers and/or tetramers, which depended on the substituents of primary aromatic amines. When 2,6-dimethylaniline or 2,6-diethylaniline was used as substrate, dimer, and tetramer were formed as major products. When 2,6-diisopropylaniline or 2,6-dihaloanilines was used as substrate, dimer, and trimer were formed. The mechanistic aspect was also investigated.

Key words: Primary aromatic amine; Oxidative coupling; Cerium sulfate