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

Priyabrata Das, Jef K. De Brabander

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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.

Original languageEnglish (US)
Pages (from-to)7646-7652
Number of pages7
JournalTetrahedron
Volume69
Issue number36
DOIs
StatePublished - Sep 9 2013

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Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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