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

被引:115
作者
Campbell, EJ [1 ]
Nguyen, ST [1 ]
机构
[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA
基金
美国国家卫生研究院;
关键词
D O I
10.1016/S0040-4039(00)02226-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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. Tn 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. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1221 / 1225
页数:5
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