ArticleNature chemistry2019
The reductive C3 functionalization of pyridinium and quinolinium salts through iridium-catalysed interrupted transfer hydrogenation.
Article in Nature chemistry, 2019. 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.
- Asymmetric Reductive Three-Component Annulation Reaction for Constructing Fused N-Heterocycles With Contiguous Stereogenic Centers.Angewandte Chemie (International ed. in English) · 2026Article
- Dearomative Cyclization of Ynamides toward the Formation of Fused Diazabicycles.Organic letters · 2025Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Functionalization of Pyridines at the C4 Position via Metalation and Capture.Angewandte Chemie (International ed. in English) · 2025Article
- Reaction strategies for the meta-selective functionalization of pyridine through dearomatization.Molecular diversity · 2025Review
- Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.Chemical reviews · 2024Review
- Oxidative Dearomatization of Pyridines.Journal of the American Chemical Society · 2024Article
- Modular synthesis of unsaturated aza-heterocycles via copper catalyzed multicomponent cascade reaction.iScience · 2023Article
- Metal and Activating Group Free C-4 Alkylation of Isoquinolines via a Temporary Dearomatization Strategy.Organic letters · 2023Article
- Recent advances in the dearomative functionalisation of heteroarenes.Chemical science · 2022Review
- Exploiting Coordination Effects for the Regioselective Zincation of Diazines Using TMPZnX⋅LiX (X=Cl, Br).Angewandte Chemie (International ed. in English) · 2022Article
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Article
- Evolution of the Dearomative Functionalization of Activated Quinolines and Isoquinolines: Expansion of the Electrophile Scope.Angewandte Chemie (International ed. in English) · 2022Article
- Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis.Nature communications · 2022Article
- Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives.Chemical science · 2021Article
- Interrupted reactions in chemical synthesis.Nature reviews. Chemistry · 2021Review
- Iridium Complex-Catalyzed Transfer Hydrogenation of N-Heteroarenes and Tentative Asymmetric Synthesis.ACS omega · 2021Article
- Heterocyclic group transfer reactions with I(iii)Chemical science · 2021Article
- Modular synthesis of chiral 1,2-dihydropyridines via Mannich/Wittig/cycloisomerization sequence that internally reuses waste.Nature communications · 2021Article
- Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
6 authors.
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Abstract
Aromatic rings are ubiquitous in organic chemistry and form the basis of many commercial products. Despite the numerous routes available for the preparation of aromatic compounds, there remain few methods that allow their conversion into synthetically useful partially saturated derivatives and even fewer that allow new C-C bonds to be formed at the same time. Here we set out to address this problem and uncover a unique catalytic partial reduction reaction that forms partially saturated azaheterocycles from aromatic precursors. In this reaction, methanol and formaldehyde are used for the reductive functionalization of pyridines and quinolines using catalytic iridium; thus, inexpensive and renewable feedstocks are utilized in the formation of complex N-heterocycles. By harnessing the formation of a nucleophilic enamine intermediate, the C-C bond-forming process reverses the normal pattern of reactivity and allows access to the C3 position of the arene. Mechanistic investigations using D-labelling experiments reveal the source of hydride added to the ring and show the reversible nature of the iridium-hydride addition.
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Registered trials
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