ArticleChemical science2024
How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes.
Article in Chemical science, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- moTSart: accelerating automated transition state search with generative models in a low-data regime.Digital discovery · 2026Article
- Synthesis of Macrocyclic Structures by Intramolecular Photoclick Reaction.Journal of the American Chemical Society · 2026Article
- Insights into Tetrazine-Benzene Cycloadditions.The journal of physical chemistry. A · 2026Article
- strainedSMILES2xyz: a workflow for reliable 3D structures of strained molecules from SMILES.Journal of cheminformatics · 2026Article
- Influence of Cycloalkane Carboxylic Acid Ring Size on Tribological Properties of TiN Coatings Under Lubricated Conditions.Materials (Basel, Switzerland) · 2026Article
- Signature of click chemistry in advanced techniques for cancer therapeutics.RSC advances · 2025Review
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
Corrections and comments
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Authors and funding
5 authors.
Funding
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Abstract
Dibenzoannulated cyclooctynes have emerged as valuable compounds for bioorthogonal reactions. They are commonly used in combination with azides in strain-promoted 1,3-dipolar cycloadditions. They are typically, however, unreactive towards 3,6-disubstituted tetrazines in inverse electron-demand Diels-Alder cycloadditions. Recently a dibenzoannulated bicyclo[6.1.0]nonyne derivative (DMBO) with a cyclopropane fused to the cyclooctyne core was described, which showed surprising reactivity towards tetrazines. To elucidate the unusual reactivity of DMBO, we performed density functional theory calculations and revealed that a tub-like structure in the transition state results in a much lower activation barrier than in the absence of cyclopropane fusion. The same transition state geometry is found for different cycloalkanes fused to the cyclooctyne core albeit higher activation barriers are observed for increased ring sizes. This conformation is energetically unfavored for previously known dibenzoannulated cyclooctynes and allows tetrazines and azides to approach DMBO from the face rather than the edge, a trajectory that was hitherto not observed for this class of activated dieno- and dipolarophiles.
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Registered trials
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