5'-substituted-6-carboxylic-2,2'-bipyridine acid: a pivotal architecton for building preorganized ligands.
A set of ligands bearing 6-bromo-2,2'-bipyridine pendant arms attached in the 5'-position are described. Transformation of the bromo to an ester was performed by a carboethoxylation reaction promoted by low-valent Pd(0), while saponification followed by acidification gave the acids. The introduction of an appended function 3-nitrobenzyl, benzamidomethyl, and tert-butylacetyl opens the way to further functionalize these scaffolds for potential labeling of biological material. The synthetic protocols represent a valuable approach to the rational design of ligands bearing oxophilic and anionic sidearms.
Charbonnière
Loïc J
LJ
Laboratoire de Chimie Moléculaire, Associé au CNRS UMR-7008, Ecole de Chimie, Polymères et Matériaux de Strasbourg (ECPM), 25 rue Becquerel, 67087 Strasbourg Cedex 02, France.
Weibel
Nicolas
N
Ziessel
Raymond F
RF
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D008163:Luminescent Measurements
D002264:Carboxylic Acids; D007202:Indicators and Reagents; D008024:Ligands; D015082:2,2'-Dipyridyl