A room temperature copper catalyzed N-selective arylation of β-amino alcohols with iodoanilines and aryl iodides

TETRAHEDRON

卷:69

Article

Das, Priyabrata¹  De Brabander, Jef K.¹ 

[1] Univ Texas SW Med Ctr Dallas, Dept Biochem, Dallas, TX 75390 USA

关键词: Cross-coupling;    Copper catalysis;    Arylation;    Amino Alcohol;    Iodoaniline;    Benzimidazole;   

DOI  :  10.1016/j.tet.2013.04.128

来源: Elsevier

【 摘 要 】

An efficient method is described for the synthesis of N-(2-aminophenyl)-2-hydroxyethylamines via a copper catalyzed N-selective arylation of beta-amino alcohols with iodoanilines. The corresponding coupling products are useful intermediates for the synthesis of a variety of N-2-hydroxyethyl-substituted benzimidazoles, benzimidazolones, and iminobenzimidazoles. We found that 2-iodoaniline only arylates certain amino alcohols but not amines lacking a hydroxyl group. We also demonstrate the arylation of sterically demanding beta-amino alcohols, such as ephedrine and prolinol with aryl iodides at room temperature. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free