ArticleNature communications2023
Dearomative triple elementalization of quinolines driven by visible light.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Photoinduced Hydrogenative Dearomatization With Homocoupling of Quinolines to Construct Octahydro-4,4'-biquinolines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Single Photocatalytic Hydrosilylation of Alkenes for the Synthesis of Bis(silyl) and Silaboryl Alkanes.JACS Au · 2025Article
- Development of a Highly Selective Synthesis of 4-Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Recent advances and perspectives in synthetic applications of silylboronates as silyl radical precursors.Chemical science · 2025Review
- Photochemical dearomative skeletal modifications of heteroaromatics.Chemical Society reviews · 2024Review
- Vibration-mediated long-wavelength photolysis of electronegative bonds beyond SCommunications chemistry · 2024Article
Corrections and comments
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Authors and funding
8 authors.
Funding
Abstract
Organoboron and organosilicon compounds are used not only as synthetic building blocks but also as functional materials and pharmaceuticals, and compounds with multiple boryl and silyl groups are beginning to be used for these purposes. Especially in drug discovery, methodology providing easy stereoselective access to aliphatic nitrogen heterocycles bearing multiple boryl or silyl groups from readily available aromatic nitrogen heterocycles would be attractive. However, such transformations remain challenging, and available reactions have been mostly limited to dearomative hydroboration or hydrosilylation reactions. Here, we report the dearomative triple elementalization (carbo-sila-boration) of quinolines via the addition of organolithium followed by photo-boosted silaboration, affording the desired products with complete chemo-, regio-, and stereoselectivity. The reaction proceeds via the formation of silyl radicals instead of silyl anions. We also present preliminary studies to illustrate the potential of silaboration products as synthetic platforms.
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Registered trials
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