ArticleACS catalysis2019
Heteroarene Phosphinylalkylation via a Catalytic, Polarity-Reversing Radical Cascade.
Article in ACS catalysis, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Biomimetic 1,2-amino migration via photoredox catalysis.Nature chemistry · 2025Article
- Radical Polarity.Journal of the American Chemical Society · 2024Article
- Metal-organic framework boosts heterogeneous electron donor-acceptor catalysis.Nature communications · 2023Article
- Radical chain monoalkylation of pyridines.Chemical science · 2021Article
- Highly Efficient Production of Heteroarene Phosphonates by Dichromatic Photoredox Catalysis.ACS applied materials & interfaces · 2021Article
- Radical philicity and its role in selective organic transformations.Nature reviews. Chemistry · 2021Review
- Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.Journal of the American Chemical Society · 2020Article
- Oxidative Generation of Boron-Centered Radicals in Carboranes.Journal of the American Chemical Society · 2020Article
- Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents.Nature communications · 2019Article
- Transition metal-free phosphonocarboxylation of alkenes with carbon dioxide via visible-light photoredox catalysis.Nature communications · 2019Article
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Authors and funding
4 authors.
Funding
Abstract
A polarity-reversing radical cascade strategy for alkene di-functionalization by vicinal C-C and C-P bond-formation has been developed. This approach to concurrently adding phosphorous and a heteroarene across an olefin is enabled by photocatalytic generation of electrophilic P-centered radicals. Upon chemoselective addition to an olefin, the resulting nucleophilic C-centered radical selectively combines with electrophilic heteroarenes, such as pyridines. This multi-component coupling scheme for phosphinylalkylation complements classic two-component methods for hydrophosphinylation of alkenes and C-H phosphinylation of arenes. Included competition and photo-quenching experiments provide insight into the selectivity and mechanism of this polarity-reversal pathway.
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