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 language | English (US) |
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Pages (from-to) | 7646-7652 |
Number of pages | 7 |
Journal | Tetrahedron |
Volume | 69 |
Issue number | 36 |
DOIs | |
State | Published - Sep 9 2013 |
Keywords
- Alcohol
- Amino
- Arylation
- Benzimidazole
- Copper catalysis
- Cross-coupling
- Iodoaniline
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry