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

E. Joseph Campbell, Sonbinh T. Nguyen

Research output: Contribution to journalArticlepeer-review

114 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)1221-1225
Number of pages5
JournalTetrahedron Letters
Volume42
Issue number7
DOIs
StatePublished - Feb 12 2001

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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