Guanidine Chemistry and Catalytic Synthesis
Summary
Guanidine derivatives occupy a prominent position in modern synthetic chemistry owing to their unique combination of basicity, hydrogen-bonding capacity and structural versatility. The C(NH2)3+ core can be introduced by a range of catalytic strategies, including metal-mediated guanylation of amines and photoredox-driven activation of carbodiimides, delivering both linear and cyclic guanidines in high selectivity. Advances in catalyst design have afforded protocols that operate under mild conditions with broad substrate tolerance, enabling late-stage functionalisation of complex molecules. Such methods underpin the rapid generation of guanidine scaffolds for applications in medicinal chemistry, materials science and organometallic ligand development. Ongoing efforts focus on improving atom economy, stereocontrol and the use of earth-abundant metals to meet sustainability goals.
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Guanidine Chemistry and Catalytic Synthesis publication trend
The graph below shows the total number of articles in guanidine chemistry and catalytic synthesis across all publications each year (not limited to Nature Index journals).
Technical terms
Guanidine: A nitrogen-rich functional group with formula C(NH2)3+, known for strong basicity and capacity to form multiple hydrogen bonds.
Guanylation: The introduction of a guanidine moiety into a substrate, typically via reaction of amines with carbodiimides or similar electrophiles.
Photoredox catalysis: A process in which light-activated catalysts mediate single-electron transfer events to drive chemical transformations under mild conditions.
Organometallic ligand: A ligand containing a metal–carbon or metal–heteroatom bond, which coordinates to a metal centre to modulate reactivity and selectivity.
References
- Guanylation Reactions for the Rational Design of Cancer Therapeutic Agents. International Journal of Molecular Sciences (2023).
- De novo design and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions. Chemical Science (2021).
- Guanidinates as Alternative Ligands for Organometallic Complexes. Molecules (2022).
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