ArticleJournal of the American Chemical Society2021
Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 29 citations in OpenAlex.
- Photo-Triggered, Fast, and Fluorogenic Thiophene-Based Cycloalkynes for the Bioorthogonal Fluorescent Labeling of 1,3-Dipole-Tagged Molecules in No-Wash Conditions.Angewandte Chemie (International ed. in English) · 2026Article
- The interplay between the pyramidalization of carbonyl carbons and the n → π* interactions in biomolecules.Protein science : a publication of the Protein Society · 2026Article
- Accessing trifluoromethylated SuFEx-able pyrazoleRSC advances · 2025Article
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes.Chemical science · 2024Article
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
- Uncovering the Key Role of Distortion in Bioorthogonal Tetrazine Tools That Defy the Reactivity/Stability Trade-Off.Journal of the American Chemical Society · 2022Article
- SuFExableThe Journal of organic chemistry · 2022Article
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
The 1,3-dipolar cycloaddition between azides and alkynes provides new means to probe and control biological processes. A major challenge is to achieve high reaction rates with stable reagents. The optimization of alkynyl reagents has relied on two strategies: increasing strain and tuning electronics. We report on the integration of these strategies. A computational analysis suggested that a CH → N aryl substitution in dibenzocyclooctyne (DIBO) could be beneficial. In transition states, the nitrogen of 2-azabenzo-benzocyclooctyne (ABC) engages in an n→π* interaction with the C=O of α-azidoacetamides and forms a hydrogen bond with the N-H of α-diazoacetamides. These dipole-specific interactions act cooperatively with electronic activation of the strained π-bond to increase reactivity. We found that ABC does indeed react more quickly with α-azidoacetamides and α-diazoacetamides than its constitutional isomer, dibenzoazacyclooctyne (DIBAC). ABC and DIBAC have comparable chemical stability in a biomimetic solution. Both ABC and DIBO are accessible in three steps by the alkylidene carbene-mediated ring expansion of commercial cycloheptanones. Our findings enhance the accessibility and utility of 1,3-dipolar cycloadditions and encourage further innovation.
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