Unsymmetrical salen-type ligands: high yield synthesis of salen-type Schiff bases containing two different benzaldehyde moieties

✍ Scribed by E.Joseph Campbell; SonBinh T Nguyen

• Book ID: 104211720
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 85 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)02226-7

✦ Synopsis

Salen-type Schiff base ligands incorporating two different benzylidene moieties and a diamine backbone were synthesized in high yield (80-90%) under mild conditions via a stepwise approach. In the first step, anhydrous hydrochloric acid was used to selectively protect one amino group of the vicinal diamine backbone. The resulting ammonium salt was added to a substituted benzaldehyde providing access to a mono-imine product. This compound reacted with an equivalent of a different benzaldehyde in the presence of triethylamine to afford an unsymmetrical salen-type ligand. This synthetic method allows facile access to a plethora of salen-type Schiff base ligands with easily tunable steric and electronic properties.