Synthetic approaches to mixed ligand chelators on tert-butylphenol-formaldehyde oligomer (PFO) platforms

TETRAHEDRON

卷:68

Article

Young, Jennifer A.¹  Karmakar, Sukhen¹  Jacobs, Hollie K.¹  Gopalan, Aravamudan S.¹ 

[1] New Mexico State Univ, Dept Chem & Biochem, Las Cruces, NM 88003 USA

关键词: tert-Butylphenol-formaldehyde oligomers;    Metal ion chelators;    Hydroxypyridinone;    Hydroxamic acid;   

DOI  :  10.1016/j.tet.2012.09.032

来源: Elsevier

【 摘 要 】

Synthetic approaches to mixed ligand chelators on readily available tert-butylphenol-formaldehyde oligomer, PFO, scaffolds were examined. In a promising approach, tris and tetraphenol oligomers were selectively mono or di protected using tert-butyldiphenyl silyl chloride. The utility of these protected intermediates to prepare representative mixed PFO chelators, carrying ligands such as hydroxamic acid, 3,2-hydroxypyridinones, and others was then demonstrated. The introduction of the ligand tethers onto the phenolic scaffold can be done sequentially under relatively mild conditions that tolerate the presence of other sensitive ligand groups. The differential reactivity of the disilyl derivative 20b, allowed stepwise introduction of two different ligands on the internal phenolic positions. This enabled the introduction of three different ligand groups of choice onto the tetraphenol platform. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

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