ArticleJournal of the American Chemical Society2017
Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 28 papers.
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Who cites it
28 citing papers in PubMed.
- Accessing trifluoromethylated SuFEx-able pyrazoleRSC advances · 2025Article
- Mutually Orthogonal Bioorthogonal Reactions: Selective Chemistries for Labeling Multiple Biomolecules Simultaneously.Topics in current chemistry (Cham) · 2024Review
- Computational Organic Chemistry: The Frontier for Understanding and Designing Bioorthogonal Cycloadditions.Topics in current chemistry (Cham) · 2024Review
- Smart Biointerfaces via Click Chemistry-Enabled Nanopatterning of Multiple Bioligands and DNA Force Sensors.ACS applied materials & interfaces · 2024Article
- How cycloalkane fusion enhances the cycloaddition reactivity of dibenzocyclooctynes.Chemical science · 2024Article
- Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Glutathione Mediates Control of Dual Differential Bio-orthogonal Labelling of Biomolecules.Angewandte Chemie (International ed. in English) · 2023Article
- Kinetically-driven reactivity of sulfinylamines enables direct conversion of carboxylic acids to sulfinamides.Chemical science · 2023Article
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
- Tricomponent Decarboxysulfonylative Cross-Coupling Facilitates Direct Construction of Aryl Sulfones and Reveals a Mechanistic Dualism in the Acridine/Copper Photocatalytic System.ACS catalysis · 2022Article
- Functional group divergence and the structural basis of acridine photocatalysis revealed by direct decarboxysulfonylation.Chemical science · 2022Article
- SuFExableThe Journal of organic chemistry · 2022Article
- Photoinduced C(spChemical science · 2021Article
- Acceleration of 1,3-Dipolar Cycloadditions by Integration of Strain and Electronic Tuning.Journal of the American Chemical Society · 2021Article
- Enzyme-mediated bioorthogonal technologies: catalysts, chemoselective reactions and recent methyltransferase applications.Current opinion in biotechnology · 2021Review
- Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.Chemical science · 2021Article
- Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.Journal of the American Chemical Society · 2020Article
- Aziridinium Ylides: Underutilized Intermediates for Complex Amine Synthesis.Trends in chemistry · 2020Article
- Live Monitoring of Strain-Promoted Azide Alkyne Cycloadditions in Complex Reaction Environments by Inline ATR-IR Spectroscopy.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
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5 authors.
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Abstract
The ability to achieve predictable control over the polarization of strained cycloalkynes can influence their behavior in subsequent reactions, providing opportunities to increase both rate and chemoselectivity. A series of new heterocyclic strained cyclooctynes containing a sulfamate backbone (SNO-OCTs) were prepared under mild conditions by employing ring expansions of silylated methyleneaziridines. SNO-OCT derivative 8 outpaced even a difluorinated cyclooctyne in a 1,3-dipolar cycloaddition with benzylazide. The various orbital interactions of the propargylic and homopropargylic heteroatoms in SNO-OCT were explored both experimentally and computationally. The inclusion of these heteroatoms had a positive impact on stability and reactivity, where electronic effects could be utilized to relieve ring strain. The choice of the heteroatom combinations in various SNO-OCTs significantly affected the alkyne geometries, thus illustrating a new strategy for modulating strain via remote substituents. Additionally, this unique heteroatom activation was capable of accelerating the rate of reaction of SNO-OCT with diazoacetamide over azidoacetamide, opening the possibility of further method development in the context of chemoselective, bioorthogonal labeling.
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