ArticleChemical science2022
Synthesis of complex bicyclic scaffolds by intermolecular photosensitized dearomative cycloadditions of activated alkenes and naphthalenes.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Probing Into Asymmetric Dearomatizing Photocycloadditions of 2-Naphthalene Derivatives With Alkenes: [2 + 2] and [4 + 2] Pathways.Angewandte Chemie (International ed. in English) · 2026Article
- Substrate-Controlled Dearomative Cycloadditions of Perfluoronaphthalenes via Visible-Light Energy Transfer Catalysis: Switchable Access to [2+2], [4+2], and Diastereoconvergent Cycloadducts.Angewandte Chemie (International ed. in English) · 2026Article
- [2+2] Photocycloaddition reactions of sulfinylamines with alkenes to access β-sultam derivatives.Nature chemistry · 2026Article
- Accessing Medium-Sized Bridged Heterocycles via EnT-Catalyzed Intermolecular Dearomative (5 + 4) Cycloaddition of Furans and Oxazoles.Journal of the American Chemical Society · 2026Article
- Triple energy transfer-enabled dearomative cycloaddition/rearrangement cascade of bicyclic azaarenes to structurally complex products.Nature catalysis · 2026Article
- Light-Mediated Binaphthyl Enhanced [2 + 2] Dearomatization of Heterocycles via an Energy-Transfer Process.Organic letters · 2025Article
- Ligand-Controlled Regioselective Dearomative Vicinal and Conjugate Hydroboration of Quinolines.Journal of the American Chemical Society · 2025Article
- Visible light-driven dearomative meta-cycloadditions of 2-acetonaphthalenes via triplet energy transfer cascade.Nature communications · 2025Article
- Boron Enabled Directed [2+2]- and Dearomative [4+2]-Cycloadditions Initiated by Energy Transfer.Angewandte Chemie (International ed. in English) · 2025Article
- Three-dimensional saturated C(spNature reviews. Chemistry · 2024Review
- Stereoselective polar radical crossover for the functionalization of strained-ring systems.Communications chemistry · 2024Article
- Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes.Nature communications · 2024Article
- Photo-induced intramolecular dearomative [5 + 4] cycloaddition of arenes for the construction of highly strained medium-sized-rings.Nature communications · 2024Article
- Visible-Light-Promoted Tandem Skeletal Rearrangement/Dearomatization of Heteroaryl Enallenes.Molecules (Basel, Switzerland) · 2024Article
- Photochemical Reduction of Quinolines with γ-Terpinene.Organic letters · 2024Article
- Synthesis of 2-Azanorbornanes via Strain-Release Formal Cycloadditions Initiated by Energy Transfer.Angewandte Chemie (International ed. in English) · 2023Article
- Rejuvenation of dearomative cycloaddition reactionsChemical science · 2023Review
- Photosensitized [4+2]- and [2+2]-Cycloaddition Reactions of N-Sulfonylimines.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
4 authors.
Funding
Abstract
The rapid buildup of molecular complexity from simple precursors is a key goal in organic chemistry. One strategy to achieve this is through a dearomative cycloaddition wherein a 2D arene and alkene is converted to a 3D structure. In many cases this type of reactivity has been achieved with photochemistry. Despite the prospect of such a reaction, most known variants are intramolecular, which greatly limits the scope of chemical space that can be accessed. Intermolecular variants are known but are generally limited to heterocyclic systems such as indoles or quinolines. Herein, a method for intermolecular dearomative cycloaddition of simple naphthalenes with alkenes is presented. The reactions operate by a photoinduced sensitization of the arene. The bridged bicyclic products are generated with control of regiochemistry and function for a range of alkenes. In addition, the products can serve as useful intermediates as demonstrated in the synthesis of a biologically active benzazapine analog. Mechanistic studies are also included, which support reaction
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