ArticleJournal of the American Chemical Society2025
Divergent Synthesis of 1-Azabicyclo[n.1.1]alkane Bioisosteres via Photoinduced Palladium Catalysis.
Article in Journal of the American Chemical Society, 2025. 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.
- On-DNA photochemical methods for expanding DNA-encoded library (DEL) chemical space.RSC medicinal chemistry · 2026Review
- Modular synthesis of functionalized azetidines through visible-light copper-catalyzed carboamination of 1,3-dienes with azabicyclo[1.1.0]butanes.Chemical science · 2026Article
- Strain Release of 1-Azabicyclo[1.1.0]butanes as a Gateway to Highly Functionalized Azetidines: New Strategies and Structural Motifs.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- A general photoinduced manganese-catalyzed platform for the sequential difunctionalization of [1.1.1]propellane.Science advances · 2026Article
- Visible Light-Induced Synthesis of Isoquino[2,1-a]pyrimidine Derivatives Catalyzed by Covalent Triazine Frameworks.Chemistry, an Asian journal · 2026Article
- Boron-Enabled Stereoselective Synthesis of Polysubstituted Housanes.Journal of the American Chemical Society · 2025Article
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Authors and funding
6 authors.
Funding
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Abstract
Nitrogen heterocycles are indispensable structural motifs in pharmaceuticals, agrochemicals, and materials science. However, the development of new synthetic methods to access these frameworks remains a significant challenge. Here, we describe a switchable radical approach for the synthesis of 1-azabicyclo[2.1.1]hexanes and 1-azabicyclo[4.1.1]octenes through the coupling of azabicyclo[1.1.0]butanes with 1,3-dienes, mediated by a visible-light-driven palladium photocatalytic system. This method exhibits a broad substrate scope, excellent functional group compatibility, and the capacity to assemble complex architectures, underscoring its utility in accessing valuable aza-bioisosteres. The strategy has also been employed successfully in DNA-encoded library (DEL) synthesis. Mechanistic studies, synthetic applications, and computational analyses corroborate the proposed open-shell pathway, revealing that allylic palladium intermediate formation and regiodivergent nucleophilic addition are key to achieving divergent synthesis.
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Registered trials
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