ArticleJournal of the American Chemical Society2019
Enantioselective [2+2] Cycloadditions of Cinnamate Esters: Generalizing Lewis Acid Catalysis of Triplet Energy Transfer.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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Who cites it
56 citing papers in PubMed, 202 citations in OpenAlex.
- Excitation of acyclic trisubstituted alkenes via triplet energy transfer for diastereo- and enantioselective [2 + 2] photocycloaddition.Nature communications · 2026Article
- N-Aryl Acridone Derivatives as Effective Catalysts for Energy Transfer Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Reenvisioning the De Mayo Reaction: A Boron-Enabled Cycloaddition Approach.Angewandte Chemie (International ed. in English) · 2026Article
- Bifunctional Photocatalysts: Exploiting Proximity for Enhanced Reaction Performance.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Catalytic Enantioselective [6π] Photocyclization Reactions by Chromophore Activation with a Chiral Lewis Acid.Journal of the American Chemical Society · 2025Article
- Essential oil-derived decomposable polymers via cycloaddition polymerization of silyl ether-linked phenylpropanoids.Nature communications · 2025Article
- A Bifunctional Organic Photocatalyst for Efficient Single-Electron and Energy Transfer Activation.Angewandte Chemie (International ed. in English) · 2025Article
- Pathway-divergent coupling of alkynes and cyclobutenes through enantioselective cobalt catalysis.Nature communications · 2025Article
- Understanding the Mechanism of Triplet-Triplet Energy Transfer in the Photocatalytic [2 + 2] Cycloaddition: Insights From Quantum Chemical Modeling.Journal of computational chemistry · 2025Article
- Cooperative Photoredox Catalysis Under Confinement.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Chemistry of 2-(2'-Aminophenyl)benzothiazole Derivatives: Syntheses, Photophysical Properties and Applications.Molecules (Basel, Switzerland) · 2025Review
- Palladium-Catalyzed Alkoxycarbonylation of Alcohols for the Synthesis of Cyclobutanecarboxylates with α-Quaternary Carbon Centers.Organic letters · 2025Article
- Boron Enabled Directed [2+2]- and Dearomative [4+2]-Cycloadditions Initiated by Energy Transfer.Angewandte Chemie (International ed. in English) · 2025Article
- Light-enabled intramolecular [2 + 2] cycloaddition via photoactivation of simple alkenylboronic esters.Beilstein journal of organic chemistry · 2025Article
- Article
- Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone.Nature communications · 2024Article
- Recent advances in the application of [2 + 2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products.Natural products and bioprospecting · 2024Review
- Catalytic asymmetric [4 + 2] dearomative photocycloadditions of anthracene and its derivatives with alkenylazaarenes.Nature communications · 2024Article
- Photosensitized [2 + 2]-Cycloadditions of Dioxaborole: Reactivity Enabled by Boron Ring Constraint Strategy.Journal of the American Chemical Society · 2023Article
- Iterative Dual-Metal and Energy Transfer Catalysis Enables Stereodivergence in Alkyne Difunctionalization: Carboboration as Case Study.ACS catalysis · 2023Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
We report the enantioselective [2+2] cycloaddition of simple cinnamate esters, the products of which are useful synthons for the controlled assembly of cyclobutane natural products. This method utilizes a cocatalytic system in which a chiral Lewis acid accelerates the transfer of triplet energy from an excited-state Ir(III) photocatalyst to the cinnamate ester. Computational evidence indicates that the principal role of the Lewis acid cocatalyst is to lower the absolute energies of the substrate frontier molecular orbitals, leading to greater electronic coupling between the sensitizer and substrate and increasing the rate of the energy transfer event. These results suggest Lewis acids can have multiple beneficial effects on triplet sensitization reactions, impacting both the thermodynamic driving force and kinetics of Dexter energy transfer.
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