ArticleChemistry (Weinheim an der Bergstrasse, Germany)2014
Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
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- Isocampholenic Acid Derivatives as Potential Fragrances.Molecules (Basel, Switzerland) · 2025Article
- Structure-activity relationships in the development of single atom catalysts for sustainable organic transformations.Nanoscale advances · 2025Review
- Oxidative [3+2]Cycloaddition of Alkynylphosphonates with HeterocyclicMolecules (Basel, Switzerland) · 2022Article
- FunctionalizedMolecules (Basel, Switzerland) · 2022Article
- On-Surface Azide-Alkyne Cycloaddition Reaction: Does It Click with Ruthenium Catalysts?Langmuir : the ACS journal of surfaces and colloids · 2022Article
- Synthesis of 3,4,5-trisubstituted isoxazoles in water via a [3 + 2]-cycloaddition of nitrile oxides and 1,3-diketones, β-ketoesters, or β-ketoamides.Beilstein journal of organic chemistry · 2022Article
- Facile synthesis ofRSC advances · 2021Article
- Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.Chemical reviews · 2021Review
- Ligand-Based Design of Allosteric Retinoic Acid Receptor-Related Orphan Receptor γt (RORγt) Inverse Agonists.Journal of medicinal chemistry · 2020Article
- Synthesis of C4-alkynylisoxazolesRSC advances · 2019Article
- The synthetic and therapeutic expedition of isoxazole and its analogs.Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents · 2018Review
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Authors and funding
3 authors.
Funding
Abstract
(Cyclopentadienyl)(cyclooctadiene) ruthenium(II) chloride [CpRuCl(cod)] catalyzes the reaction between nitrile oxides and electronically deficient 1-choro-, 1-bromo-, and 1-iodoalkynes leading to 4-haloisoxazoles. Organic azides are also suitable 1,3-dipoles, resulting in 5-halo-1,2,3-triazoles. These air-tolerant reactions can be performed at room temperature with 1.25 equivalents of the respective 1,3-dipole relative to the alkyne component. Reactive 1-haloalkynes include propiolic amides, esters, ketones, and phosphonates. Post-functionalization of the halogenated azole products can be accomplished by using palladium-catalyzed cross-coupling reactions and by manipulation of reactive amide groups. The lack of catalysis observed with [Cp*RuCl(cod)] (Cp* = pentamethylcyclopentadienyl) is attributed to steric demands of the Cp* (η(5)-C5Me5) ligand in comparison to the parent Cp (η(5)-C5H5). This hypothesis is supported by the poor reactivity of [(η(5)-C5Me4CF3)RuCl(cod)], which serves as a an isosteric mimic of Cp* and as an isoelectronic analogue of Cp.
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