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Synthesis of mono-, bis- and tris-tridentate ligands based on 5′-substituted-2,2′-bipyridine-6-carboxylic acid

✍ Scribed by Loı̈c J Charbonnière; Nicolas Weibel; Raymond F Ziessel

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 85 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)02033-5

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✦ Synopsis

The synthesis of 5%-methyl-2,2%-bipyridine-6-carboxylic acid is described starting from the pivotal 5%-methyl-6-bromo-2,2%-bipyridine building block. Functionalisation of the latest at the 5%-methyl position gives access to the 5%-bromomethyl, 5%-hydroxymethyl and 5%-aminomethyl derivatives. Upon nucleophilic substitution, the hydroxy and amino derivatives react with the 5%-bromomethyl compound to give quasi-linear and podand type intermediates. Thanks to a carboalkoxylation reaction at the 6-bromo position of the different intermediates, followed by a saponification reaction, mono-, bis-and tris-tridentate ligands are obtained, which are particularly well suited for the complexation of lanthanide(III) cations.

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