4392-87-4

Usage

Uses

Used in Chemical Research:
2,2'-Bipyridine-6-carboxylic acid is used as a research chemical compound for various applications in the field of chemistry. It is particularly useful in the development of new chemical reactions and the synthesis of complex organic molecules.
Used in Regioselective Remote Hydrocarbofunctionalization:
In the Engle lab, 2,2'-bipyridine-6-carboxylic acid has been developed as a key component in regioselective remote hydrocarbofunctionalization of alkene-containing substrate classes. It works in conjunction with a similar ligand, PAQ (901250), to enable Pd(II) catalysis for the selective functionalization of alkenes in various substrates, such as 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamines. This selective functionalization is crucial for the synthesis of complex organic molecules and the development of new chemical reactions.

Upstream product

• 4392-85-2 2,2'-bipyridyl-6-carbonitrile 

Downstream Products

• 156100-94-6 2,2′-bipyridine-6-carbonyl chloride 

Relevant academic research and scientific papers

Regioselective functionalization of 2,2′-bipyridine and transformations into unsymmetric ligands for coordination chemistry

Novel synthetic strategies for a series of unsymmetrically substituted 2,2′-bipyridines have been developed. These bipyridines have found use in some novel homoleptic and heteroleptic ruthenium(II) complexes. Two methods for regiochemical control of nucleophilic addition to bpy have been explored: (i) mono N-oxidation followed by cyanation and subsequent hydrolysis gave 6-carboxy-2,2′-bipyridine (4); (ii) mono N-methylation followed by the conversion into 6-bromo-2,2′-bipyridine (12) and subsequent nucleophilic addition of lithioacetonitrile followed by hydrolysis of 6-cyanomethyl-2,2′-bipyridine (8) gave the homologous 2,2′-bipyridine-6-acetic acid (9). An established method of regioselective mono-ring alkylation of bpy using methyllithium yielded 6-methyl-2,2′-bipyridine (14), and the generation of the anion of 14 and subsequent addition to a chloromethyl oxazoline was applied to synthesize a second homologue, methyl 2,2′-bipyridine-6-propanoate (16). Structural determinations using 1H, 13C and 2D NMR spectroscopy permitted complete assignments of all signals in the 1H NMR spectra. Acta Chemica Scandinavica 1998.