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

Research paper by Priyabrata P Das, Jef K JK De Brabander

Indexed on: 17 Sep '13Published on: 17 Sep '13Published in: Tetrahedron



Abstract

An efficient method is described for the synthesis of N-(2-aminophenyl)-2-hydroxyethylamines via a copper catalyzed N-selective arylation of β-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 β-amino alcohols, such as ephedrine and prolinol with aryl iodides at room temperature.