ArticleJournal of the American Chemical Society2015
1,3-Dipolar cycloaddition reactivities of perfluorinated aryl azides with enamines and strained dipolarophiles.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 112 citations in OpenAlex.
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- Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism.The Journal of organic chemistry · 2024Article
- The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.Chemistry, an Asian journal · 2022Review
- Selective Synthesis of AzoloylACS omega · 2022Article
- Accessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary.The Journal of organic chemistry · 2021Article
- Synthesis, crystal structure and Hirshfeld surface analysis of (4-methyl-phen-yl)[1-(penta-fluoro-phen-yl)-5-(tri-fluoro-meth-yl)-1Acta crystallographica. Section E, Crystallographic communications · 2021Article
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- Imaging, Identification and Inhibition of Microorganisms Using AIEgens.Topics in current chemistry (Cham) · 2021Review
- A cascade reaction of cinnamyl azides with vinyl sulfones directly generates dihydro-pyrrolo-pyrazole heterocycles.Tetrahedron letters · 2021Article
- Quantification of binding affinity of glyconanomaterials with lectins.Chemical communications (Cambridge, England) · 2020Review
- Interfacial nanoconnections and enhanced mechanistic studies of metallic coatings for molecular gluing on polymer surfaces.Nanoscale advances · 2020Article
- A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles.The Journal of organic chemistry · 2020Article
- Access to tetracyclic aromatics with bridgehead metals via metalla-click reactions.Science advances · 2020Article
- A Versatile Catalyst-Free Perfluoroaryl Azide-Aldehyde-Amine Conjugation Reaction.Materials chemistry frontiers · 2019Article
- Synthesis of Carbohydrate-Grafted Glycopolymers Using a Catalyst-Free, Perfluoroarylazide-Mediated Fast Staudinger Reaction.Molecules (Basel, Switzerland) · 2019Article
- Experimental and Computational Study of the ( Z)-Selective Formation of Trisubstituted Olefins and Benzo-Fused Oxacycles from the Ruthenium-Catalyzed Dehydrative C-H Coupling of Phenols with Ketones.Journal of the American Chemical Society · 2018Article
- Kinetics of the Strain-Promoted Oxidation-Controlled Cycloalkyne-1,2-quinone Cycloaddition: Experimental and Theoretical Studies.The Journal of organic chemistry · 2018Article
- Perfluoroaryl Azide Staudinger Reaction: A Fast and Bioorthogonal Reaction.Angewandte Chemie (International ed. in English) · 2017Article
- Design and synthesis of theranostic antibiotic nanodrugs that display enhanced antibacterial activity and luminescence.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
The reactivities of enamines and predistorted (strained) dipolarophiles toward perfluoroaryl azides (PFAAs) were explored experimentally and computationally. Kinetic analyses indicate that PFAAs undergo (3 + 2) cycloadditions with enamines up to 4 orders of magnitude faster than phenyl azide reacts with these dipolarophiles. DFT calculations were used to identify the origin of this rate acceleration. Orbital interactions between the cycloaddends are larger due to the relatively low-lying LUMO of PFAAs. The triazolines resulting from PFAA-enamine cycloadditions rearrange to amidines at room temperature, while (3 + 2) cycloadditions of enamines and phenyl azide yield stable, isolable triazolines. The 1,3-dipolar cycloadditions of norbornene and DIBAC also show increased reactivity toward PFAAs over phenyl azide but are slower than enamine-azide cycloadditions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.