Homocoupling Reactions of Azoles and Their Applications in Coordination Chemistry

Pyrazole, a member of the structural class of azoles, exhibits molecular properties of interest in pharmaceuticals and materials chemistry, owing to the two adjacent nitrogen atoms in the five-membered ring system. The weakly basic nitrogen atoms of deprotonated pyrazoles have been applied in coordi...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2020-12, Vol.25 (24), p.5950
Main Authors: Mogensen, Steffen B, Taylor, Mercedes K, Lee, Ji-Woong
Format: Article
Language:English
Subjects:
Azoles
Azoles - chemistry
bipyrazole
Carbon
Catalysis
Chemical reactions
Chemistry
Coordination polymers
Copper
Heterocyclic compounds
homocoupling
Imidazole
INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Ligands
Metal-organic frameworks
Metal-Organic Frameworks - chemical synthesis
Metal-Organic Frameworks - chemistry
Molecular Structure
Nitrogen
Nitrogen atoms
Oxidation
Polymers
Pyrazole
Pyrazoles
Pyrazoles - chemical synthesis
Pyrazoles - chemistry
Reaction mechanisms
Review
Tetrazoles
Transition metals
transition-metal catalysts
Triazoles
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Summary:Pyrazole, a member of the structural class of azoles, exhibits molecular properties of interest in pharmaceuticals and materials chemistry, owing to the two adjacent nitrogen atoms in the five-membered ring system. The weakly basic nitrogen atoms of deprotonated pyrazoles have been applied in coordination chemistry, particularly to access coordination polymers and metal-organic frameworks, and homocoupling reactions can in principle provide facile access to bipyrazole ligands. In this context, we summarize recent advances in homocoupling reactions of pyrazoles and other types of azoles (imidazoles, triazoles and tetrazoles) to highlight the utility of homocoupling reactions in synthesizing symmetric bi-heteroaryl systems compared with traditional synthesis. Metal-free reactions and transition-metal catalyzed homocoupling reactions are discussed with reaction mechanisms in detail.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules25245950