ArticleJournal of the American Chemical Society2021
Practical and Regioselective Synthesis of C-4-Alkylated Pyridines.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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Who cites it
22 citing papers in PubMed.
- Pyridine C─N Transposition via Cycloaddition-Cycloreversion.Angewandte Chemie (International ed. in English) · 2026Article
- Phosphonium Ions as Activating Groups for the Selective Alkylation of Pyridines and Polyazines.Journal of the American Chemical Society · 2026Article
- Room-temperature electrochemical hydroxyalkylation of pyridines.Nature communications · 2026Article
- Electrochemical C4 alkylation of pyridine derivatives: Enhanced regioselectivity via silane assistance.Science advances · 2025Article
- Halogenated Pyridine Derivatives from Cycloaddition / Cycloreversion of Oxazinone and Haloalkyne Precursors.Tetrahedron letters · 2025Article
- Bioinspired transfer methylation enabled by a photoactive reagent.Nature communications · 2025Article
- Late-Stage Heteroarene Alkylation via Minisci Reaction with Gaseous Alkanes Enabled by Hydrogen Atom Transfer in Flow.ACS central science · 2025Article
- Iron-catalyzed aliphatic C-H functionalization to construct carbon-carbon bonds.Nature communications · 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
- Phosphite mediated molecular editingChemical science · 2025Article
- Polysubstituted Pyridines from 1,4-Oxazinone Precursors.The Journal of organic chemistry · 2024Article
- Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.Science advances · 2024Article
- Unified ionic and radical C-4 alkylation and arylation of pyridines.Chemical science · 2024Article
- Construction of the 4-Azafluorenone Core in a Single Operation and Synthesis of Onychine.The Journal of organic chemistry · 2024Article
- Visible light-induced chemoselective 1,2-diheteroarylation of alkenes.Nature communications · 2024Article
- Article
- Recent Advances in Catalytic and Technology-Driven Radical Addition toMolecules (Basel, Switzerland) · 2023Review
- Photochemical Organocatalytic Functionalization of Pyridines via Pyridinyl Radicals.Journal of the American Chemical Society · 2023Article
- Dual role of benzophenone enables a fast and scalable C-4 selective alkylation of pyridines in flow.Chemical science · 2022Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.
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