ArticleNature chemistry2014
Atom-efficient regioselective 1,2-dearomatization of functionalized pyridines by an earth-abundant organolanthanide catalyst.
Article in Nature chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- Silylative Amide to Nitrile Conversion Mediated by Simple Lanthanide-Organoamides: Scope and Mechanism.Angewandte Chemie (International ed. in English) · 2025Article
- Trimethylaluminum Activates Zeolite-Confined Lanthanum Borohydrides to Enhance Catalytic C-H Borylation.Journal of the American Chemical Society · 2025Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Enhancing electrocatalytic hydrogen evolutionChemical science · 2025Review
- Cobalt-catalyzed double hydroboration of pyridines.Chemical science · 2024Article
- Oxidative Dearomatization of Pyridines.Journal of the American Chemical Society · 2024Article
- Synthesis and utility ofFrontiers in chemistry · 2024Review
- Mechanistic study of homoleptic trisamidolanthanide-catalyzed aldehyde and ketone hydroboration. Chemically non-innocent ligand participation.Chemical science · 2023Article
- A bis(silylene)pyridine pincer ligand can stabilize mononuclear manganese(0) complexes: facile access to isolable analogues of the elusive dChemical science · 2022Article
- s-Block Metal Catalysts for the Hydroboration of Unsaturated Bonds.Chemical reviews · 2022Review
- Nitropyridines as 2π-Partners in 1,3-Dipolar Cycloadditions with N-Methyl Azomethine Ylide: An Easy Access to Condensed Pyrrolines.Molecules (Basel, Switzerland) · 2021Article
- Aluminum Amidinates: Insights into Alkyne Hydroboration.Inorganic chemistry · 2021Article
- Manganese-Catalyzed Hydroborations with Broad Scope.Angewandte Chemie (International ed. in English) · 2021Article
- Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines.Angewandte Chemie (International ed. in English) · 2021Article
- Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.Journal of the American Chemical Society · 2020Article
- Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis.Nature communications · 2020Article
- An umpolung approach to the hydroboration of pyridines: a novel and efficient synthesis ofChemical science · 2019Article
- Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes.Chemical science · 2019Article
- Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.Chemical science · 2018Article
- Donor-influenced Structure-Activity Correlations in Stoichiometric and Catalytic Reactions of Lithium Monoamido-Monohydrido-Dialkylaluminates.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
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Authors and funding
5 authors.
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Abstract
Developing earth-abundant, non-platinum metal catalysts for high-value chemical transformations is a critical challenge to contemporary chemical synthesis. Dearomatization of pyridine derivatives is an important transformation to access a wide range of valuable nitrogenous natural products, pharmaceuticals and materials. Here, we report an efficient 1,2-regioselective organolanthanide-catalysed pyridine dearomatization process using pinacolborane, which is compatible with a broad range of pyridines and functional groups and employs equimolar reagent stoichiometry. Regarding the mechanism, derivation of the rate law from NMR spectroscopic and kinetic measurements suggests first order in catalyst concentration, fractional order in pyridine concentration and inverse first order in pinacolborane concentration, with C=N insertion into the La-H bond as turnover-determining. An energetic span analysis affords a more detailed understanding of experimental activity trends and the unusual kinetic behaviour, and proposes the catalyst 'resting' state and potential deactivation pathways.
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