ArticleChemical science2021
Pyridylphosphonium salts as alternatives to cyanopyridines in radical-radical coupling reactions.
Article in Chemical science, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Electrochemical C4 alkylation of pyridine derivatives: Enhanced regioselectivity via silane assistance.Science advances · 2025Article
- Pnictogen bonding enabled photosynthesis of chiral selenium-containing pyridines from pyridylphosphonium salts.Fundamental research · 2025Article
- CspACS catalysis · 2024Article
- Unified ionic and radical C-4 alkylation and arylation of pyridines.Chemical science · 2024Article
- 1,3-Difunctionalization of [1.1.1]propellane through iron-hydride catalyzed hydropyridylation.Nature communications · 2024Article
- Late-Stage C-H Functionalization of Azines.Chemical reviews · 2023Review
- Photochemical Organocatalytic Functionalization of Pyridines via Pyridinyl Radicals.Journal of the American Chemical Society · 2023Article
- Homolytic N-S Bond Cleavage in Vinyl Triflimides Enabled by Triplet-Triplet Energy Transfer.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Metal-free deoxygenative coupling of alcohol-derived benzoates and pyridines for small molecules and DNA-encoded libraries synthesis.Chemical science · 2022Article
- Reductant-Free Cross-Electrophile Synthesis of Di(hetero)arylmethanes by Palladium-Catalyzed Desulfinative C-C Coupling.Angewandte Chemie (International ed. in English) · 2022Article
- Uniting Amide Synthesis and Activation by PJournal of the American Chemical Society · 2021Article
Corrections and comments
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Authors and funding
3 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Radical couplings of cyanopyridine radical anions represent a valuable technology for functionalizing pyridines, which are prevalent throughout pharmaceuticals, agrochemicals, and materials. Installing the cyano group, which facilitates the necessary radical anion formation and stabilization, is challenging and limits the use of this chemistry to simple cyanopyridines. We discovered that pyridylphosphonium salts, installed directly and regioselectively from C-H precursors, are useful alternatives to cyanopyridines in radical-radical coupling reactions, expanding the scope of this reaction manifold to complex pyridines. Methods for both alkylation and amination of pyridines mediated by photoredox catalysis are described. Additionally, we demonstrate late-stage functionalization of pharmaceuticals, highlighting an advantage of pyridylphosphonium salts over cyanopyridines.
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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.