Sulfonato-Cu(salen) Complex Catalyzed N-Arylation of Aliphatic Amines with Aryl Halides in Water

• Published in: European Journal of Organic Chemistry 2010-09, Vol.2010 (26), p.4971-4975
• Main Authors: Wu, Zhiqing, Zhou, Li, Jiang, Zhaoqiong, Wu, Di, Li, Zhengkai, Zhou, Xiangge
• Format: Article
• Language: English
• Subjects: Aliphatic compounds; Amination; Catalysis; Catalysts: preparations and properties; Chemistry; Copper; Cross-coupling; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Noncondensed benzenic compounds; Organic chemistry; Preparations and properties; Sulfonates; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Water chemistry
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000840

A water‐soluble sulfonato‐Cu(salen) complex catalyzed procedure for the N‐arylation of simple aliphatic amines, amino alcohols and amino acids in pure water have been developed. A variety of substituted aryl iodides, bromides and electron‐deficient chlorides were found to be applicable, and 1,2‐disubstituted benzimidazoles could be prepared easily by a cascade amination/condensation process in this catalytic system. A protocol of water‐soluble sulfonato–Cu(salen) complex catalyzed N‐arylation of simple aliphatic amines, amino alcohols and amino acids in water has been developed. A variety of substituted aryl iodides,bromides and electron‐deficient chlorides were found to be applicable, and 1,2‐disubstituted benzimidazoles could be prepared conveniently by a cascade amination/condensation process in this catalytic system.