Functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines via stille-type cross-coupling procedures.

doi:10.1021/JO0260600

Paper

Functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines via stille-type cross-coupling procedures.

Published Oct 19, 2002 · M. Heller, U. Schubert

The Journal of organic chemistry

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Abstract

Stille-type cross-coupling procedures are utilized in order to prepare a variety of functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines. Such N-heterocyclic compounds are of great interest as chelating ligands for transition-metal ions in the field of supramolecular chemistry. Various mono- and disubstitued 2,2'-bipyridines were synthesized in high yields and multigram scales using a modular design principle. The terpyridines may be functionalized in one step with different substituents at the outer pyridine rings and at the 4'-position of the centered ring, leading to multifunctionalized compounds. The initially obtained methyl ester and ethyl ester groups can be simply converted into bromomethyl and hydroxymethyl groups which allow further functionalization reactions.

Study Snapshot

This study successfully synthesized various functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines using stille-type cross-coupling procedures, providing valuable chelating ligands for transition-metal ions in supramolecular chemistry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Functionalized 2,2'-bipyridines and 2,2':6',2' '-terpyridines via stille-type cross-coupling procedures.

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References

Citations

Coordination complexes of Bipyridines (CCBs): Chemistry, bonding and applications

CCBs show excellent stability, solubility, electrical and physiochemical properties, and selectivity, making them versatile materials for various applications in photochemistry, materials science, catalysis, medicine, environments, and surface protection.

Recent Progress on the Synthesis of Bipyridine Derivatives

Recent advances in bipyridine synthesis using metal complexes and sulfur and phosphorous compounds offer promising avenues for overcoming challenges associated with traditional catalysis methods.

Synthesis of 2-(2-Pyridyl)-2H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines.

This study presents a high-yield method for introducing 2-pyridyl substituents in 2-bromo-2H-azirine-2-carboxylic acid derivatives by direct cross-coupling with 2-(trialkylstannyl)pyridines, which can also be used

Terpyridinebenzaldehyde isomers: One-pot facile synthesis

This study presents a one-pot method for the synthesis of Terpyridinebenzaldehyde isomers using ethanol and aqueous ammonia, offering simplicity, reaction time, satisfactory yield, and easy work-up under mild reaction conditions.

The 2‐Pyridyl Problem: Challenging Nucleophiles in Cross‐Coupling Arylations

This review highlights the need for efficient methods for synthesis of pyridine-containing biaryls, focusing on traditional cross-coupling processes, alternative nucleophilic reagents, and novel main group approaches.