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

作者：Das Priyabrata; De Brabander Jef K^*

来源：Tetrahedron, 2013, 69(36): 7646-7652.

DOI：10.1016/j.tet.2013.04.128

• Cross-coupling
• Copper catalysis
• Arylation
• Amino Alcohol
• Iodoaniline
• Benzimidazole

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.

• 出版日期2013-9-9