ArticleChemical science2020
Single point activation of pyridines enables reductive hydroxymethylation.
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Formaldehyde and its surrogates as a C1 platform for defossilised modern societies.Chemical Society reviews · 2025Review
- Dearomative Cyclization of Ynamides toward the Formation of Fused Diazabicycles.Organic letters · 2025Article
- Recent Strategies in the Nucleophilic Dearomatization of Pyridines, Quinolines, and Isoquinolines.Chemical reviews · 2024Review
- Vicinal stereocentersChemical science · 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
- 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
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The single point activation of pyridines, using an electron-deficient benzyl group, facilitates the ruthenium-catalysed dearomative functionalisation of a range of electronically diverse pyridine derivatives. This transformation delivers hydroxymethylated piperidines in good yields, allowing rapid access to medicinally relevant small heterocycles. A noteworthy feature of this work is that paraformaldehyde acts as both a hydride donor and an electrophile in the reaction, enabling the use of cheap and readily available feedstock chemicals. Removal of the activating group can be achieved readily, furnishing the free NH compound in only 2 steps. The synthetic utility of the method was illustrated with a synthesis of (±)-Paroxetine.
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Registered trials
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