ArticleAngewandte Chemie (International ed. in English)2019
Exploiting Imine Photochemistry for Masked N-Centered Radical Reactivity.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Photocatalytic Stereoselective Editing of Alkynes to 3D Molecules via Hydrogen Atom Transfer-Mediated Dynamic Epimerization.Nature communications · 2026Article
- Photocatalyzed Epimerization of Quaternary Stereocenters.Journal of the American Chemical Society · 2025Article
- Modular Synthesis of Dehydroprolines by an Energy-Transfer Enabled Cloke-Wilson Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Article
- Formal Cycloadditions Driven by the Homolytic Opening of Strained, Saturated Ring Systems.Angewandte Chemie (International ed. in English) · 2023Review
- Photochemical Intermolecular [3σ + 2σ]-Cycloaddition for the Construction of Aminobicyclo[3.1.1]heptanes.Journal of the American Chemical Society · 2022Article
- A One-Pot Photochemical Method for the Generation of Functionalized Aminocyclopentanes.Organic letters · 2022Article
- Photocatalytic Late-Stage Functionalization of Sulfonamides via Sulfonyl Radical Intermediates.ACS catalysis · 2022Article
- Strain-Release [2π + 2σ] Cycloadditions for the Synthesis of Bicyclo[2.1.1]hexanes Initiated by Energy Transfer.Journal of the American Chemical Society · 2022Article
- Photochemical Formal (4 + 2)-Cycloaddition of Imine-Substituted Bicyclo[1.1.1]pentanes and Alkenes.Journal of the American Chemical Society · 2021Article
- Photochemically derived 1-aminonorbornanes provide structurally unique succinate dehydrogenase inhibitors withCell reports. Physical science · 2021Article
- Photomediated ring contraction of saturated heterocycles.Science (New York, N.Y.) · 2021Article
- Recent Advances and Outlook for the Isosteric Replacement of Anilines.ACS medicinal chemistry letters · 2020Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
This report details the development of a masked N-centered radical strategy that harvests the energy of light to drive the conversion of cyclopropylimines to 1-aminonorbornanes. This process employs the N-centered radical character of a photoexcited imine to facilitate the homolytic fragmentation of the cyclopropane ring and the subsequent radical cyclization sequence that forms two new C-C bonds en route to the norbornane core. Achieving bond-forming reactivity as a function of the N-centered radical character of an excited state Schiff base is unique, requiring only violet light in this instance. This methodology operates in continuous flow, enhancing the potential to translate beyond the academic sector. The operational simplicity of this photochemical process and the structural novelty of the (hetero)aryl-fused 1-aminonorbornane products are anticipated to provide a valuable addition to discovery efforts in pharmaceutical and agrochemical industries.
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