ArticleJournal of the American Chemical Society2014
Rh(III)-catalyzed decarboxylative coupling of acrylic acids with unsaturated oxime esters: carboxylic acids serve as traceless activators.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Article
- Cationic palladium(ii)-catalyzed synthesis of substituted pyridines from α,β-unsaturated oxime ethers.RSC advances · 2022Article
- Rh(iii)-Catalyzed [5 + 1] annulation of 2-alkenylanilides and 2-alkenylphenols with allenyl acetates.Chemical science · 2022Article
- Three-Component 1,2-Carboamidation of Bridged Bicyclic Alkenes via RhOrganic letters · 2021Article
- Hexafluoroisopropanol: the magical solvent for Pd-catalyzed C-H activation.Chemical science · 2021Review
- Rhodium(i)-catalyzed C6-selective C-H alkenylation and polyenylation of 2-pyridones with alkenyl and conjugated polyenyl carboxylic acids.Chemical science · 2019Article
- Mild complexation protocol for chiral CpChemical science · 2019Article
- Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.Accounts of chemical research · 2018Review
- DABCO- and DBU-promoted one-pot reaction ofBeilstein journal of organic chemistry · 2018Article
- A β-Carbon elimination strategy for convenientChemical science · 2017Article
- Heptamethylindenyl (Ind*) enables diastereoselective benzamidation of cyclopropenesChemical science · 2017Article
- Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.Journal of the American Chemical Society · 2017Article
- Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.Journal of the American Chemical Society · 2016Article
- Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.Organic letters · 2016Article
- Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.Organic letters · 2016Article
- Overcoming naphthoquinone deactivation: rhodium-catalyzed C-5 selective C-H iodination as a gateway to functionalized derivatives.Chemical science · 2016Article
- Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.Angewandte Chemie (International ed. in English) · 2015Article
- Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C-H Activation.Journal of the American Chemical Society · 2015Article
- Rhodium(III)-Catalyzed C-H Activation: An Oxidative Intramolecular Heck-Type Reaction Directed by a Carboxylic Acid.Synlett : accounts and rapid communications in synthetic organic chemistry · 2015Article
- Facile Rh(III)-Catalyzed Synthesis of Fluorinated Pyridines.Organic letters · 2015Article
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Authors and funding
2 authors.
Funding
Abstract
α,β-Unsaturated carboxylic acids undergo Rh(III)-catalyzed decarboxylative coupling with α,β-unsaturated O-pivaloyl oximes to provide substituted pyridines in good yield. The carboxylic acid, which is removed by decarboxylation, serves as a traceless activating group, giving 5-substituted pyridines with very high levels of regioselectivity. Mechanistic studies rule out a picolinic acid intermediate, and an isolable rhodium complex sheds further light on the reaction mechanism.
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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.